6-Chloro-1,2,3,4-Tetrahydroisoquinoline Hydrochloride → N-[2-Chloro-4-(6-chloro-3,4-dihydro-1H-isoquinolin-2-yl)-6-methyl-phenyl]-3,3-dimethylbutanamide

HRID 880686

反応式

HRID 880686 の反応式
CC(C)([O-])C.[K+].Cl.[Cl:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2.Br[C:20]1[CH:25]=[C:24]([CH3:26])[C:23]([NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[C:22]([Cl:35])[CH:21]=1>C1(C)C=CC=CC=1>[Cl:35][C:22]1[CH:21]=[C:20]([N:14]2[CH2:13][CH2:12][C:11]3[C:16](=[CH:17][CH:18]=[C:9]([Cl:8])[CH:10]=3)[CH2:15]2)[CH:25]=[C:24]([CH3:26])[C:23]=1[NH:27][C:28](=[O:34])[CH2:29][C:30]([CH3:32])([CH3:31])[CH3:33]

参加物

5

反応物 3

HCID 125950846-Chloro-1,2,3,4-Tetrahydroisoquinoline HydrochlorideHCID 23665647Potassium tert-butoxideHCID 58097339N-(4-bromo-2-chloro-6-methylphenyl)-3,3-dimethylbutanamide

生成物 1

HCID 24937206N-[2-Chloro-4-(6-chloro-3,4-dihydro-1H-isoquinolin-2-yl)-6-methyl-phenyl]-3,3-dimethylbutanamide

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Bis(dibenzylidineacetone)palladium (2 mg, 0.0035 mmol) and (2′-dicyclohexyl phosphanyl-biphenyl-2-yl)-dimethylamine (3.3 mg, 0.0084 mmol) were added to dry toluene (10 mL purged with argon) and stirred for 15 minutes under argon. Potassium tert-butoxide (197 mg, 1.75 mmol), 6-chloro-1,2,3,4-tetrahydroisoquinoline hydrochloride salt (133 mg, 0.65 mmol), and N-(4-bromo-2-chloro-6-methylphenyl)-3,3-dimethylbutanamide (200 mg, 0.63 mmol) were then added, and the reaction mixture was stirred at 90° C. overnight. The reaction mixture was then cooled to room temperature, concentrated, and purified by thin layer chromatography (dichloromethane:methanol 5%) to afford the title compound as a solid.

後処理

  1. stirringthe reaction mixture was stirred at 90° C. overnight
  2. concentrationconcentrated
  3. custompurified by thin layer chromatography (dichloromethane:methanol 5%)

出典と根拠

ORDレコード
ord-6a2bb95053034ce9b03f4d4780bc3356
出典データセット
uspto-grants-2015_03
特許番号
US08993593B2

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