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

HRID 241625ノート

反応式

HRID 241625 の反応式
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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5af3856ebcb0446fba28d821b758d005
出典データセット
uspto-grants-2014_02
特許番号
US08653072B2

反応ノート

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