Sodium hydride → HCID 67272082, 화합물

HRID 1023166

반응식

HRID 1023166 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[H-].[Na+].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:7](=[O:12])[CH:6]=[CH:5]2

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 123789436-Bromoquinolin-2(1H)-one

생성물 1

HCID 67272082HCID 67272082, 화합물수율 80%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 6-bromoquinolin-2(1H)-one (2 g, 8.92 mmol) in DMF (20 mL) was added NaH (0.26 g, 10.7 mmol) at 0° C. After stirring for 30 min, 1-(chloromethyl)-4-methoxybenzene (1.67 g, 10.7 mmol) was added and the resulting reaction mixture was stirred at RT overnight. The reaction mixture was diluted with water and the precipitate was filtered, washed with water and dried. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give 6-bromo-1-(4-methoxybenzyl)quinolin-2(1H)-one as yellow solid (2.4 g, 80%). 1HNMR: 400 MHz, DMSO-d6: δ 3.70 (s, 3H), 5.43 (s, 2H), 6.78 (d, J=9.60 Hz, 1H), 6.87 (dd, J=2.00, 6.40 Hz, 2H), 7.14 (d, J=8.80 Hz, 2H), 7.38 (d, J=8.80 Hz, 1H), 7.66 (dd, J=2.40, 8.80 Hz, 1H), 7.94 (d, J=−8.40 Hz, 1H), 8.01 (d, J=2.40 Hz, 1H).

후처리

  1. customthe resulting reaction mixture
  2. stirringwas stirred at RT overnight
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude product was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-992b80b66c134eafa232b5455bad1807
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722670B2

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