Sodium hydride → HCID 86679725、化合物

HRID 77440ノート

反応式

HRID 77440 の反応式
[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

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 125201446-Bromo-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 86679725HCID 86679725、化合物収率 76.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ffd31b84476e4888adadf7a90b84ac49
出典データセット
uspto-grants-2014_09
特許番号
US08841301B2

反応ノート

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