Acetonitrile → 3-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(5-methyl-pyrazin-2-yl)-butan-2-ol

HRID 1097857노트

반응식

HRID 1097857 반응식
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[N:25][C:24]([CH3:27])=[CH:23][N:22]=1)=[O:20].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC#N>C1COCC1.C(O)(C(F)(F)F)=O>[Cl:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]([CH3:28])[C:19]([C:21]1[CH:26]=[N:25][C:24]([CH3:27])=[CH:23][N:22]=1)([OH:20])[C:2]([F:4])([F:3])[F:1]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 552549(Trifluoromethyl)trimethylsilaneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 666991162-(2-Chloro-4-methoxy-phenyl)-1-(5-methyl-pyrazin-2-yl)-propan-1-one

생성물 1

HCID 252527573-(2-Chloro-4-methoxy-phenyl)-1,1,1-trifluoro-2-(5-methyl-pyrazin-2-yl)-butan-2-ol수율 24.1%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8028Tetrahydrofuran용매

실험 절차

Trifluoromethyltrimethylsilane (2N in THF, 0.6 mL, 1.2 mmol) was added at 0° C. to a solution of 2-(2-chloro-4-methoxy-phenyl)-1-(5-methyl-pyrazin-2-yl)-propan-1-one (290 mg, 1.0 mmol) in THF (7 mL), followed by the addition of tetrabutylammonium fluoride trihydrate (31 mg, 0.1 mmol). After stirring overnight at r.t., the title compound (87 mg, 24%) was isolated from the reaction mixture by reversed-phase, preparative HPLC (Agilent Zorbax XdB-C18 column, solvent gradient 5-95% CH3CN in 0.1% TFA[aq]). 1H NMR (300 MHz, CDCl3) □ 8.75 (1H, s), 8.13 (1H, s), 7.44 (1H, d), 6.64 (1H, d), 6.59 (1H, dd), 5.90 (1H, s), 4.33 (1H, q), 3.67 (3H, s), 2.50 (3H, s), 1.54 (3H, d); MS (m/e, ISP neg. ion)=359.1 [M−H+].

출처 및 근거

ORD 기록
ord-e3c60a4ea4fd4eac93ce65fd6024ad92
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143280B2

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