Water → HCID 44466356, compound

HRID 241624Notes

Reaction equation

HRID 241624 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:22]3[CH:27]=[CH:26][C:25]([O:28]C)=[CH:24][CH:23]=3)[C:9]3[C:14]([C:15]=2[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:30])[O:4][N:3]=1.B(Br)(Br)Br.O.O1CCOCC1>C(Cl)Cl>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:22]3[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=3)[C:9]3[C:14]([C:15]=2[C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:30])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 312751,4-DioxaneHCID 58378239HCID 58378239, compound

Product 1

HCID 44466356HCID 44466356, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone was dissolved in dry DCM and the mixture was cooled on an ice-bath under an atmosphere of nitrogen. BBr3 (17 μl, 0.1 mmol) was added and the temperature was allowed to warm to RT and the mixture was stirred over night. Water, DCM and some dioxane were added, the phases were separated and the solvents were evaporated. The residue was passed through a short plug of silica with EtOAc as eluent. The residue was purified by preparative HPLC to provide the title compound 1-(2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl)-2,2,2-trifluoroethanone in 46% yield. ES/MS m/z: 401.1 (M+H), 399.1 (M−H); 1H NMR (methanol-d4, 500 MHz): 8.26 (m, 1H), 7.41-7.34 (m, 2H), 7.18 (m, 1H), 7.11 (m, 2H), 6.89 (m, 2H), 2.19 (s, 31-1) and 2.01 (s, 3H).

Workup

  1. temperaturethe mixture was cooled on an ice-bath under an atmosphere of nitrogen
  2. customthe phases were separated
  3. customthe solvents were evaporated
  4. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9fec8487ae23489ea083f8249cc4cfd8
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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