Sodium hydride → HCID 86679725, compound

HRID 77440Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17]>CN(C=O)C.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[C:7](=[O:12])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6-bromo-1,8-naphthyridin-2(1H)-one (0.1 g, 0.444 mmol) in DMF (2 mL) was added sodium hydride (0.021 g, 0.889 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, then SEM-Cl (0.118 mL, 0.667 mmol) was added. The reaction was stirred at room temperature overnight, then diluted with ammonium chloride solution, extracted with ethyl acetate, dried over Na2SO4, and concentrated. The crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether to give 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1,8-naphthyridin-2(1H)-one (0.12 g, 76%). 1HNMR 400 MHz (CDCl3): 0.034 (s, 9H), 0.95-0.99 (m, 2H), 3.73-3.77 (m, 2H), 5.92 (s, 2H), 6.75-6.77 (m, 1H), 7.56-7.58 (m, 1H), 7.96-7.98 (m, 1H), 8.63-8.64 (m, 1H).

Workup

stirringThe reaction was stirred at room temperature overnight
extractionextracted with ethyl acetate
dry with materialdried over Na2SO4
concentrationconcentrated
customThe crude product was purified by flash chromatography on silica gel using 20% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-ffd31b84476e4888adadf7a90b84ac49
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841301B2

Reaction notes

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