Benzene → 2,4-Dichlorobenzoyl chloride

HRID 2177650

反応式

HRID 2177650 の反応式
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]

参加物

8

反応物 6

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

生成物 2

HCID 666452,4-Dichlorobenzoyl chloride収率 52%HCID 904095952-ethyl-1-phenyl-1H-imidazo[4,5-c]pyridine収率 25%

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-03aa78ecac6f469996ac905835467438
出典データセット
uspto-grants-2015_06
特許番号
US09066946B2

関連ノート

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