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Phthalic Anhydride → 3-[N-(2-carboxybenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 1886456
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HRID 1886456 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]1(=[O:36])[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12>CN(C=O)C>[C:29]([C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[C:26]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:36])([OH:31])=[O:30]
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참가 물질

5

반응물 3

HCID 6811Phthalic AnhydrideHCID 24758Sodium hydrideHCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

생성물 1

HCID 100268683-[N-(2-carboxybenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the product of Step A (75 mg, 0.25 mmol) in 3 mL of DMF was added 11 mg (0.27 mmol, 1.1 eq) of 60% NaH, followed by 45 mg (0.30 mmol, 1.2 eq) of phthalic anhydride. This mixture was stirred for 16 hours and the DMF removed in vacuo. The resultant oil was flash column chromatographed with 15% of (10/1) mixture of methanol/NH4OH in CHCl3 to yield the titled compound (53 mg, 47%).

후처리

  1. customthe DMF removed in vacuo
  2. customchromatographed with 15% of (10/1) mixture of methanol/NH4OH in CHCl3

출처 및 근거

ORD 기록
ord-802584dede6348459bae1151ee9896a0
출처 데이터셋
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05151435

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