Diisopropylethylamine → HCID 86648964, 화합물

HRID 449929

반응식

HRID 449929 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 86648964HCID 86648964, 화합물수율 53.4%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c2f844975da0402cbe3c51f97dd0fb00
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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