Trifluoroborane-methyl sulfide → 4-[3-bromo-2-(3,5-dimethylisoxazol-4-yl)-1H-indole-1-yl]phenol

HRID 241625노트

반응식

HRID 241625 반응식
B(F)(F)F.CSC.[Br:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)[C:10]=1[C:26]1[C:27]([CH3:32])=[N:28][O:29][C:30]=1[CH3:31]>C(Cl)Cl.CCOC(C)=O>[Br:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)[C:10]=1[C:26]1[C:27]([CH3:32])=[N:28][O:29][C:30]=1[CH3:31]

참가 물질

5

반응물 2

HCID 11137191Trifluoroborane-methyl sulfideHCID 583782244-(3-bromo-1-(4-methoxyphenyl)-1H-indol-2-yl)-3,5-dimethylisoxazole

생성물 1

HCID 444663574-[3-bromo-2-(3,5-dimethylisoxazol-4-yl)-1H-indole-1-yl]phenol

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

At 0° C., 10 eq of boron trifluoride-dimethyl sulfide was added to 4-[3-bromo-1-(4-methoxyphenyl)-1H-indol-2-yl]-3,5-dimethylisoxazole (the intermediate product of step (b) from the synthesis of Example 22), dissolved in DCM and stirred at ambient temperature over night. The mixture was diluted with EtOAc and washed with brine, the organic phase was concentrated and subjected to reversed phase preparative HPLC. Appropriate fractions were combined and evaporated, and identified by ES/MS m/z: 385.1 (M+H), 383.09 (M−H) and 1H NMR (acetone-d6, 500 MHz): 7.60 (m, 1H), 7.31-7.23 (m, 3H), 7.17 (m, 2H), 6.95 (m, 2H), 2.28 (s, 3H) and 1.99 (s, 3H).

후처리

  1. customfrom the synthesis of Example 22),
  2. washwashed with brine
  3. concentrationthe organic phase was concentrated
  4. customevaporated

출처 및 근거

ORD 기록
ord-5af3856ebcb0446fba28d821b758d005
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653072B2

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