Water → 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)-2-phenylacetamide

HRID 556316

반응식

HRID 556316 반응식
[H-].[Na+].[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[N:8][CH:9]=1.Br[CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23]([NH2:25])=[O:24].O>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7](=[N:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[N:8]([CH:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([NH2:25])=[O:24])[CH:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2420282-Bromo-2-phenylacetamideHCID 57607460N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide

생성물 1

HCID 669921912-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)-2-phenylacetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (0.040 g, 0.0017 mol) was suspended in N,N-dimethylformamide (15 mL) and was cooled at 0° C. N-(5-fluoropyridin-2-yl)-4-methylbenzenesulfonamide (compound a, 0.37 g, 0.0014 mol) was added and was stirred for 15 minutes. 2-Bromo-2-phenylacetamide h (0.3 g, 0.001 mol) was added then the reaction was warmed to room temperature and was stirred for 24 hours. The reaction was poured into water and extracted with ethyl acetate (3×50 mL) then dried then chromatographed on silica (50% ethyl acetate/hexanes) to give 2-(5-fluoro-2-(tosylimino)pyridin-1(2H)-yl)-2-phenylacetamide (compound j) Rf 0.42, 50% ethyl acetate/hexanes; MS m/z 400 (M+H).

후처리

  1. temperaturethe reaction was warmed to room temperature
  2. stirringwas stirred for 24 hours
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. customthen dried
  5. customthen chromatographed on silica (50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-74db22c0fa98482bb673e0b92276941c
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058274B2

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