Triethylamine → 2-[3-Methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole

HRID 7748ノート

反応式

HRID 7748 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:10][C:9]=1[O:23][CH3:24].C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:23][C:9]1[CH:10]=[C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:12]=[CH:13][C:8]=1[CH2:7][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 219909912-[4-(Bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole

生成物 1

HCID 102365762-[3-Methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Pyrrolidine (226 μL, 2.83 mmol) was added to a stirring solution of 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole (300 mg, 0.94 mmol) and triethylamine (390 μL, 2.8 mmol) in CH2Cl2 (5 mL). The mixture was stirred at rt overnight. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford the desired 2-[3-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-benzoxazole as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 7.82–7.80 (m, 1H), 7.77–7.74 (m, 1H), 7.71 (s, 1H), 7.56–7.50 (m, 2H), 7.35–7.30 (m, 2H), 3.94 (s, 3H), 3.71 (s, 2H), 2.59 (s, 4H), 1.81–1.78 (m, 4H). MS (ESI) 309 (M+H)+.

後処理

  1. custompurified by automated flash chromatography

出典と根拠

ORDレコード
ord-8d727bc8a4d84ea78c9269287c4a100c
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

反応ノート

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