Water → HCID 44466355, compound

HRID 383460Notes

Reaction equation

HRID 383460 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([S:18]([CH3:21])(=[O:20])=[O:19])=[C:10]2[C:22]2[C:23]([CH3:28])=[N:24][O:25][C:26]=2[CH3:27])=[CH:5][CH:4]=1.B(Br)(Br)Br.O.CCOC(C)=O>C(Cl)Cl>[CH3:28][C:23]1[C:22]([C:10]2[N:9]([C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)[C:17]3[C:12]([C:11]=2[S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][CH:14]=[CH:15][CH:16]=3)=[C:26]([CH3:27])[O:25][N:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 58378229HCID 58378229, compound

Product 1

HCID 44466355HCID 44466355, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(1-(4-Methoxyphenyl)-3-(methylsulfonyl)-1H-indol-2-yl)-3,5-dimethylisoxazole was dissolved in 2 ml of dry DCM and cooled to −78° C. under nitrogen. BBr3 (31 μl, 0.33 mmol) was added and the temperature was allowed to warm to RT for 2 h. Water and EtOAc were added and the phases were separated. After evaporation of the solvents, the residue was purified by preparative HPLC to provide 4-[2-(3,5-dimethyl-isoxazol-4-yl)-3-methanesulfonyl-indol-1-yl]-phenol in 27% yield. ES/MS m/z: 383.11 (M+H), 381.13 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.12 (m, 1H), 7.39-7.34 (m, 2H), 7.25-7.19 (m, 3H), 6.98 (m, 2H), 3.06 (s, 3H), 2.30 (s, 3H) and 2.09 (s, 3H).

Workup

  1. temperatureto warm to RT for 2 h
  2. customthe phases were separated
  3. customAfter evaporation of the solvents
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9764bc4861164a6e9d19db1f0684eaf0
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

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