Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-one

HRID 226937노트

반응식

HRID 226937 반응식
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([CH:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[F:24])[CH2:10]1)=[O:8]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

생성물 1

HCID 668968333-(3,4-dimethyl-benzoyl)-1-(2-fluoro-benzyl)-2,3-dihydro-1H-quinolin-4-one수율 20.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In 3 mL of anhydrous dimethylformamide was suspended 16 mg (0.4 mmol) of sodium hydride (60%), 86 mg (0.31 mmol) of 3-(3,4-dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a was added and the mixture was stirred at rt. After 30 minutes, 75.6 mg (0.40 mmol) of 2-fluorobenzylbromide was added and the reaction was stirred at room temperature for 1 hour. The reaction mixture was quenched by the addition of 10 mL of water. The crude product precipitated out were isolated by filtration and purified by flash chromatography to yield 25 mg of colorless solid 41: LC-MSD, m/z for C25H20FNO2 [M+H]+=386.4, [M+2H]+=387.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.526 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.2-2.3 (d, 6H), 5.7 (s, 2H), 7.1-7.3 (m, 4H), 7.3-7.4 (m, 1H), 7.4-7.5 (m, 2H),7.54 (s, 1H), 7.6-7.66 (d, 1H), 7.67-7.74 (t, 1H), 8.2 (d, 1H), 8.58 (s, 1H).

후처리

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 1 hour
  3. customThe reaction mixture was quenched by the addition of 10 mL of water
  4. customThe crude product precipitated out
  5. customwere isolated by filtration
  6. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-ac7ee47fca1d44daa19fbcd6fd68c2ee
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557213B2

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