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

HRID 241625Notes

Reaction equation

HRID 241625 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-5af3856ebcb0446fba28d821b758d005
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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