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Cesium fluoride → (R)-1-(3-methoxy-4-(oxiran-2-ylmethoxy)phenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

HRID 1044415
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HRID 1044415 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)=[CH:10][C:9]2=[O:24])=[CH:4][C:3]=1[O:25][CH3:26].[F-].[Cs+].[N+](C1C=C(S(O[CH2:42][C@H:43]2[CH2:45][O:44]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.C(Cl)Cl>[CH3:26][O:25][C:3]1[CH:4]=[C:5]([N:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[CH:16][CH:15]=3)=[CH:10][C:9]2=[O:24])[CH:6]=[CH:7][C:2]=1[O:1][CH2:42][C@H:43]1[CH2:45][O:44]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 671350841-(4-hydroxy-3-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one

생성물 1

HCID 86660698(R)-1-(3-methoxy-4-(oxiran-2-ylmethoxy)phenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one수율 73.1%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

실험 절차

A mixture of 1-(4-hydroxy-3-methoxyphenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one Part B of Procedure 14 (38 mg, 0.105 mmol) and cesium fluoride (48 mg, 0.32 mmol) in DMF (1 mL) was stirred at RT for 30 min. Then, (R)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (35 mg, 0.13 mmol) was added and stirred overnight at RT. Diluted with DCM, washed with water, sat. NaHCO3, dried (Na2SO4), and concentrated. The crude was purified using ISCO flash chromatography (silica gel/hexanes/ethyl acetate 100:0 to 0:100 gradient) to afford the desired product (R)-1-(3-methoxy-4-(oxiran-2-ylmethoxy)phenyl)-4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one 15A (32.1 mg, 0.08 mmol, 73.1% yield) as a light yellow solid. LC/MS 418 (M+H)+, tR 0.93 min (method 5).

후처리

  1. stirringstirred overnight at RT
  2. washwashed with water, sat. NaHCO3
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude was purified

출처 및 근거

ORD 기록
ord-1cfbb85858284c9283cce7901be4540f
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08563583B2

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