Boron tribromide → HCID 57595739, compound

HRID 1964978Notes

Reaction equation

HRID 1964978 reaction equation
C(OC([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[C:11]2[C:10]([C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29]C)[C:24]=2[F:31])=[CH:9]1)=O)(C)(C)C.B(Br)(Br)Br>C(Cl)Cl>[F:31][C:24]1[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:23]=1[C:22]([C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[NH:8][CH:9]=1)=[O:32]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58086316HCID 58086316, compound

Product 1

HCID 57595739HCID 57595739, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-(2-fluoro-3-methoxy-benzoyl)-5-thiophen-2-yl-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester (87, 200 mg, 0.44 mmol) in methylene chloride (10 mL), under an atmosphere of nitrogen, cooled in a −78° C. acetone/dry ice bath, was added boron tribromide (1.0 M in hexane, 2.0 mL). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with methanol (3.0 mL), poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The desired compound was isolated by silica gel column chromatography eluting with 5% methanol in methylene chloride to give a white solid (P-0521, 119 mg, 82.6%). MS(ESI)[M−H+]−=337.

Workup

  1. customThe reaction was quenched with methanol (3.0 mL)
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a67de8f177514e33ae7c387e12eec5f1
Source dataset
uspto-grants-2013_04
Patent number
US08415469B2

Reaction notes

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