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

HRID 7748노트

반응식

HRID 7748 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+.

후처리

  1. custompurified by automated flash chromatography

출처 및 근거

ORD 기록
ord-8d727bc8a4d84ea78c9269287c4a100c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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