Boron tribromide → HCID 44470373, compound

HRID 2382949Notes

Reaction equation

HRID 2382949 reaction equation
C[O:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:34]=[CH:33][C:12]([CH2:13][NH:14][C:15]([C:17]2[C:18]3[CH:19]=[N:20][N:21]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:22]=3[CH:23]=[CH:24][CH:25]=2)=[O:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7].B(Br)(Br)Br>ClCCl>[OH:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:15]([C:17]2[C:18]3[CH:19]=[N:20][N:21]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[C:22]=3[CH:23]=[CH:24][CH:25]=2)=[O:16])=[CH:33][CH:34]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 44470084HCID 44470084, compound

Product 1

HCID 44470373HCID 44470373, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a chilled (−78° C.) solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid 4-(2-methoxy-ethylsulfamoyl)-benzylamide (22 mg, 0.45 mmol) in dichloromethane (5 mL) was added in several portions a 1 M solution of BBr3 (0.13 mL, 0.13 mmol) in dichloromethane. The mixture was allowed to warm to room temperature. The mixture was quenched with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (2×5 mL), dried over magnesium sulfate, filtered and concentrated. The material was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in hexanes to afford the title compound as a white powder.

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with brine (2×5 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by silica gel chromatography
  8. washeluting with a gradient of 0-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-89e025f1e03445aca9d28767dd0a27a5
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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