Benzene → 2,4-Dichlorobenzoyl chloride

HRID 2177650

반응식

HRID 2177650 반응식
CC(NC(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](C(F)(F)F)[C:8]=1[Cl:17])C#C.N1[N:23]2[CH:24]=[CH:25][CH:26]=[N:27][C:22]2=[N:21]N=1.[Cl:28][C:29]1[CH:37]=[C:36](F)[CH:35]=[CH:34][C:30]=1[C:31]([Cl:33])=[O:32].[CH3:39][CH2:40]N(C(C)C)C(C)C.[CH:48]1C=CC=C[CH:49]=1.C(Br)C=C>>[Cl:28][C:29]1[CH:37]=[C:36]([Cl:17])[CH:35]=[CH:34][C:30]=1[C:31]([Cl:33])=[O:32].[CH2:48]([C:22]1[N:27]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:26]2[CH:25]=[CH:24][N:23]=[CH:40][C:39]=2[N:21]=1)[CH3:49]

참가 물질

8

반응물 6

HCID 241BenzeneHCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 349391Tetrazolo(1,5-a)pyrimidineHCID 27365462-Chloro-4-fluorobenzoyl chlorideHCID 90409423N-(1-Methylpropargyl)-2-chloro-3-(trifluoromethyl)benzamide

생성물 2

HCID 666452,4-Dichlorobenzoyl chloride수율 52%HCID 904095952-ethyl-1-phenyl-1H-imidazo[4,5-c]pyridine수율 25%

실험 절차

To the suspension of compound Intermediate 233 (138 mg, 0.5 mmol, 1.0 equiv), tetrazolo[1,5-a]pyrimidine (Intermediate 234) (67 mg, 0.55 mmol, 1.1 equiv.) and Hunig's base (0.3 mL, 1.75 mmol, 3.5 equiv.), (CuOTf)2.Benzene (150 mg, 0.6 mmol, 1.2 equiv.) was added at room temperature in one portion under N2. After 6 hours at room temperature, HPLC analysis indicated the complete consumption of Intermediate 233. Allyl bromide (242 mg, 2.0 mmol, 4.0 equiv.) was added and the reaction solution was stirred for another 2 hours. The same workup/purification procedure were followed to afford Intermediate 235 (113 mg, 0.26 mml, 52% yield) along with Intermediate 236 (49 mg, 0.12 mmol, 25% yield).

후처리

  1. customthe complete consumption of Intermediate 233
  2. customThe same workup/purification procedure

출처 및 근거

ORD 기록
ord-03aa78ecac6f469996ac905835467438
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09066946B2

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