Diisopropylethylamine → HCID 86648964、化合物

HRID 449929

反応式

HRID 449929 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Br:8])[CH:3]=1.C(N(C(C)C)CC)(C)C.[Cl:18][C:19]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[C:24]([F:30])[C:20]=1[C:21](Cl)=[O:22]>ClCCl.CC#N>[Br:8][C:4]1[CH:3]=[C:2]([NH:1][C:21](=[O:22])[C:20]2[C:24]([F:30])=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:19]=2[Cl:18])[CH:7]=[CH:6][N:5]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 3464554-Amino-2-bromopyridineHCID 866489652-Chloro-4-cyano-6-fluorobenzoyl chloride

生成物 1

HCID 86648964HCID 86648964、化合物収率 53.4%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a cooled (0° C.) solution of 4-amino-2-bromopyridine (346 mg, 2.0 mmol) and diisopropylethylamine (461 mg, 4.0 mmol) in dichloromethane (5 mL) and CH3CN (0.5 mL) was added a solution of 2-chloro-4-cyano-6-fluorobenzoyl chloride (484 mg, 2.2 mmol) in dichlormethane (5 mL) drop wise. The reaction mixture was warmed up to room temperature and stirred for 16 hours. The reaction was quenched with saturated NH4Cl (40 mL) and extracted with EtOAc (3×50 mL). The combined organic extractss were dried with Na2SO4 and concentrated under reduced pressure. The residue wars purified by silica gel column chromatography (0-50% EtOAc/hexane) to give N-(2-bromopyridin-4-yl)-2-chloro-4-cyano-6-fluorobenzamide as an off-white solid (379 mg, yield: 53%).

後処理

  1. customThe reaction was quenched with saturated NH4Cl (40 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic extractss were dried with Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue wars purified by silica gel column chromatography (0-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-c2f844975da0402cbe3c51f97dd0fb00
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

関連ノート

読み込み中…