Boron tribromide → N-{3-[4-(4-Cyano-3-fluoro-phenyl)-3-methyl-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-3-oxo-propyl}-3-hydroxy-benzenesulfonamide

HRID 1700176Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH2:12][CH2:11][N:10]2[C:19](=[O:34])[CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32]C)[CH:27]=2)(=[O:25])=[O:24])=[CH:5][C:4]=1[F:35])#[N:2].B(Br)(Br)Br>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]3[N:15]([CH3:18])[CH:16]=[N:17][C:13]=3[CH2:12][CH2:11][N:10]2[C:19](=[O:34])[CH2:20][CH2:21][NH:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)(=[O:25])=[O:24])=[CH:5][C:4]=1[F:35])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

N-{3-[4-(4-Cyano-3-fluoro-phenyl)-3-methyl-3,4,6,7-tetrahydro-imidazo[4,5-c]pyridin-5-yl]-3-oxo-propyl}-3-methoxy-benzenesulfonamide (0.05 g, 0.100 mmol), prepared as described in Step H, was dissolved in CH2Cl2 (2 mL) and cooled to 0° C. A 1M solution of BBr3 in CH2Cl2 (2.0 mL, 2.00 mmol) was added dropwise via syringe and stirred for 4 h. The reaction mixture was diluted with CH2Cl2 and saturated NaHCO3 solution and separated. The aqueous layer was washed with CH2Cl2 (2×), the organic layers combined, dried (Na2SO4), filtered and concentrated to give the title compound.

Workup

customseparated
washThe aqueous layer was washed with CH2Cl2 (2×)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-bd18c268c1254439a8c233c155e8156c
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350755B1

Reaction notes

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