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Cesium carbonate → N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide

HRID 931389
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HRID 931389 반응식
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6]Cl.[Br:10][C:11]1[C:12]([NH:17][C:18]([C:20]2[O:39][C:23]3=[N:24][CH:25]=[C:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)[CH:27]=[C:22]3[CH:21]=2)=[O:19])=[N:13][CH:14]=[CH:15][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:10][C:11]1[C:12]([N:17]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:9])([CH3:8])[CH3:1])[C:18]([C:20]2[O:39][C:23]3=[N:24][CH:25]=[C:26]([CH2:28][O:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=4)[CH:27]=[C:22]3[CH:21]=2)=[O:19])=[N:13][CH:14]=[CH:15][CH:16]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 90050548N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide

생성물 1

HCID 90050549N-(3-Bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)-N-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-b]pyridine-2-carboxamide

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
23 °C

실험 절차

2-Trimethylsilylethoxymethyl chloride (0.13 g, 0.81 mmol) was added to a solution of N-(3-bromopyridin-2-yl)-5-(((4-methoxybenzyl)oxy)methyl)furo[2,3-b]pyridine-2-carboxamide (0.29 g, 0.62 mmol) and cesium carbonate (0.61 g, 1.8 mmol) in DMF (6.2 mL) at 0° C. The reaction mixture was gradually warmed to 23° C. and stirred for 2 h, then partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 18% ethyl acetate in petroleum ether to give the title compound. MS: m/z=600.2 (M+1).

후처리

  1. custompartitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography on silica gel eluting with 18% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-0378942b624e469c93ec7b658112a8e5
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296750B2

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