N-(5-bromo-4-methoxy-2-methylphenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(5-bromo-4-methoxy-2-methylphenyl)acetamide
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 258.115
• InChiKey: PNZHTGLCLCATLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-4-methoxy-2-methylphenyl)acetamide 在 N-甲基吗啉 、 盐酸 、 potassium phosphate 、 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 甲烷磺酸 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 二碳酸二叔丁酯 、 氢气 、 三溴化硼 、 碳酸氢钠 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 zinc dibromide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 86.67h， 生成 N-[3-氟-4-[[1-甲基-6-(1H-吡唑-4-基)-1H-吲唑-5-基]氧基]苯基]-1-(4-氟苯基)-1,2-二氢-6-甲基-2-氧代-3-吡啶甲酰胺
  参考文献：
  名称：

  Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole

  摘要：

  The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.

  DOI：

  10.1021/op400317z
• 作为产物：
  描述：

  2-甲基-4-甲氧基苯胺 在 溴 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 N-(5-bromo-4-methoxy-2-methylphenyl)acetamide
  参考文献：
  名称：

  Route Design and Development of a MET Kinase Inhibitor: A Copper-Catalyzed Preparation of an N1-Methylindazole

  摘要：

  The synthesis of a MET kinase inhibitor in an overall yield of 22% was achieved over eight steps starting with 3-hydroxybenzaldehyde, an improvement from the initial 12-step process with a 5.4% yield. Highlights of the process chemistry design and development are a Cu-catalyzed cyclization to form an important N1-methylindazole ring, a selective nitro reduction in the presence of an aryl bromide, a late-stage Suzuki cross-coupling, and a base-promoted Boc deprotection to form the desired drug candidate.

  DOI：

  10.1021/op400317z

文献信息

• AMIDOPHENOXYINDAZOLES USEFUL AS INHIBITORS OF C-MET
  申请人：LI Tiechao

  公开号：US20100022529A1

  公开（公告）日：2010-01-28

  The present invention provides amidophenoxyindazole compounds useful in the treatment of cancer.

  这项发明提供了在癌症治疗中有用的酰胺基苯氧基吲唑化合物。
• N-ACYL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF
  申请人：Yokotani Junichi

  公开号：US20110275797A1

  公开（公告）日：2011-11-10

  An N-acyl anthranilic acid derivative represented by general formula (1) or a salt thereof is useful for prevention or treatment of diseases associated with excessive production of collagen. (In the formula, R 1 represents a carboxyl group or the like; R 2 represents a hydrogen atom or the like; R 3 represents an optionally substituted aryl group or the like; X 1 represents a carbonyl group; X 2 represents a bonding hand; X 3 represents a bonding hand; X 4 represents a bonding hand or the like; and A represents an optionally substituted phenyl group or the like.)

  通用公式（1）表示的N-酰基蒽酸衍生物或其盐对预防或治疗与胶原蛋白过度产生相关的疾病具有用处。（在该公式中，R1代表羧基或类似物；R2代表氢原子或类似物；R3代表可选择取代的芳基或类似物；X1代表羰基；X2代表连接手；X3代表连接手；X4代表连接手或类似物；A代表可选择取代的苯基或类似物。）
• Practical and regioselective brominations of aromatic compounds using tetrabutylammonium peroxydisulfate
  作者：Min Young Park、Seung Gak Yang、Vidyadhar Jadhav、Yong Hae Kim

  DOI：10.1016/j.tetlet.2004.04.112

  日期：2004.6

  Direct bromination of wide range of aromatic compounds substituted with electron donating groups such as methoxy, hydroxy, or amino groups have been achieved with high regioselectivity by the reaction with Br2 in the presence of tetrabutylammonium peroxydisulfate 1 under mild conditions in acetonitrile in excellent yields. The use of lithium bromide as a bromination reagent afforded high yields of

  的宽范围内具有供电子基团，如甲氧基，羟基或氨基取代的芳族化合物的直接溴化已通过与溴反应以高区域选择性实现2在四丁基过氧存在1温和的条件下在乙腈以优良产率。使用溴化锂作为溴化试剂，可在中性和温和的反应条件下，在乙腈中获得高收率的一溴化合物，具有完全的区域选择性。
• [EN] AMIDOPHENOXYINDAZOLES USEFUL AS INHIBITORS OF C-MET<br/>[FR] COMPOSÉS AMIDO-PHÉNOXY-INDAZOLE UTILISÉS COMME INHIBITEURS DU C-MET
  申请人：LILLY CO ELI

  公开号：WO2010011538A1

  公开（公告）日：2010-01-28

  The present invention provides amidophenoxyindazole compounds useful in the treatment of cancer.

  本发明提供了一种在癌症治疗中有用的酰胺基苯氧基吲唑化合物。
• Amidophenoxyindazoles useful as inhibitors of c-Met
  申请人：Eli Lilly and Company

  公开号：US08030302B2

  公开（公告）日：2011-10-04

  The present invention provides amidophenoxyindazole compounds useful in the treatment of cancer.

  本发明提供了在癌症治疗中有用的酰胺基苯氧基吲唑化合物。