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 931389Notes

Reaction equation

[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

Participants

Conditions

Temperature: 23 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-0378942b624e469c93ec7b658112a8e5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296750B2

Reaction notes

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