Sodium hydride → HCID 178490686, 화합물

HRID 78535

반응식

HRID 78535 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7]([NH:9][C:10]1[S:11][C:12]([CH3:15])=[CH:13][N:14]=1)=[O:8].[H-].[Na+].Br[CH2:22][C:23]1[O:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH3:18])=[C:6]([CH:16]=1)[C:7](/[N:9]=[C:10]1\[S:11][C:12]([CH3:15])=[CH:13][N:14]\1[CH2:22][C:23]1[O:24][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:27]=1)=[O:8]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 26781445-chloro-2-methoxy-N-(5-methyl-1,3-thiazol-2-yl)benzamideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furan

생성물 1

HCID 178490686HCID 178490686, 화합물수율 32.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of Example 340A (0.1 g, 0.36 mmol) in 5 mL DMF was added sodium hydride (0.01 g, 0.39 mmol, 95%). The solution was allowed to stir at ambient temperature for 30 min when 2-(bromomethyl)-5-(trifluoromethyl)furan (0.09 g, 0.39 mmol) was added. The reaction was held at ambient temperature overnight and then quenched with water. The crude was extracted with ethyl acetate and the organics washed with water, then dried over MgSO4, filtered, and concentrated. Flash chromatography over silica gel (50% ethyl acetate/hexane) gave 0.05 g of the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.28 (d, J=1.36 Hz, 3H) 3.78 (s, 3H) 5.47 (s, 2H) 6.66 (d, J=2.71 Hz, 1H) 7.11 (d, J=8.81 Hz, 1H) 7.22 (dd, J=3.39, 1.36 Hz, 1H) 7.31-7.39 (m, J=1.36 Hz, 1H) 7.41-7.52 (m, 1H) 7.72 (d, J=2.71 Hz, 1H). m/z 431.0 (M+H)+.

후처리

  1. additionwas added
  2. customquenched with water
  3. extractionThe crude was extracted with ethyl acetate
  4. washthe organics washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ca9a4cfb645472fa09ff1253df89873
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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