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Sodium hydride → 6-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile

HRID 227139
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HRID 227139 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]1[N:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:27][C:28]4[N:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][CH:29]=4)[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

생성물 1

HCID 577546116-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile수율 17.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide
용매

실험 절차

The mixture of 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one (70 mg, 0.228 mmol, 1 eq) in DMF (1 ml) and sodium hydride (11.8 mg, 0.296 mmol, 1.3 eq) was stirred at room temperature for 60 min, followed by the addition of 6-Bromomethyl-pyridine-2-carbonitrile (74.1 mg, 0.296 mmol, 1.3 eq). The mixture was stirred for 60 min, quenched with water, taken up with ethyl acetate, dried over sodium sulfate and purified with flash chromatography to give the desired product (17 mg). LCMS observed for (M+H)+: 424.1.

후처리

  1. stirringThe mixture was stirred for 60 min
  2. customquenched with water
  3. dry with materialdried over sodium sulfate
  4. custompurified with flash chromatography

출처 및 근거

ORD 기록
ord-dd3947a494ca4d669105e116c3033a27
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557213B2

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