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Sodium hydride → 4'-[(2-butyl-1H-thieno[3,4-d]imidazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylic acid t-butyl ester

HRID 373609
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HRID 373609 반응식
[CH2:1]([C:5]1[NH:9][C:8]2=[CH:10][S:11][CH:12]=[C:7]2[N:6]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:15]([O:19][C:20]([C:22]1[C:23]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=2)=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>CN(C=O)C.[Cl-].[Na+].O>[C:15]([O:19][C:20]([C:22]1[C:23]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][N:9]3[C:8]4=[CH:10][S:11][CH:12]=[C:7]4[N:6]=[C:5]3[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:30][CH:29]=2)=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16]
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참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 193706342-butyl-1H-thieno[3,4-d]imidazole

생성물 1

HCID 538482894'-[(2-butyl-1H-thieno[3,4-d]imidazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylic acid t-butyl ester수율 68%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 57417360
Sodium chloride; water
용매

실험 절차

To a stirred solution of 2-butyl-1H-thieno-[3,4-d]imidazole (38 mg, 0.211 mmol) in DMF (1.6 mL) at room temperature was added NaH (316 mmol). After 30 minutes, tert-butyl-4'-bromomethylbiphenyl-2-carboxylate (80.5 mg, 0.232 mmol) was added in one portion. The reaction mixture was stirred for 2 hours and brine (5 mL) was added. Extractive workup (EtOAc) and purification by flash chromatography (SiO2, 40% EtOAc/hexane) gave 64 mg (68%) of 4'-[(2-butyl-1H-thieno[3,4-d]imidazol-1-yl)methyl][1,1'-biphenyl]-2-carboxylic acid t-butyl ester as a thick oil: 1H NMR (300 MHz, CDCl3) δ 7.78 (dd, 1H, J=7.5 and 1 Hz), 7.48 (td, 1H J=7.5 and 1 Hz), 7.40 (td, 1H, J=7.5 and 1 Hz) 7.32-7.26 (m, 3H), 7.19 (d, 2H, J=8 Hz), 6.99 (d, 1H, J=2.5 Hz), 6.28 (d, 1H, J=2.5 Hz), 5.17 (s, 2H), 2.78 (t, 2H, J=8 Hz), 1.91-1.81 (m, 2H), 1.54-1.41 (m, 2H), 1.23 (s, 9H), 0.96 (t, 3H, J=7 Hz).

후처리

  1. customExtractive workup (EtOAc) and purification by flash chromatography (SiO2, 40% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-b9b42584baec4edc8be5c76a90db7b80
출처 데이터셋
uspto-grants-1992_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05164407

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