Water → N-[4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]methanesulfonamide

HRID 252539Notes

Reaction equation

[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:12]C)=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=1)#[N:2].B(Br)(Br)Br.O>C(Cl)Cl>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:20][CH:21]=1)#[N:2]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of N-[4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl]methanesulfonamide (85 mg, 0.23 mmol) in CH2Cl2 (2 mL) is cooled to −5° C. A solution of boron tribromide (1.15 mL, 1.15 mmol, 1M solution in CH2Cl2) is added and the reaction mixture is allowed to warm to 10° C. over 4 h. The reaction mixture is poured into H2O and extracted with EtOAc (3×). The combined organic phases are washed with H2O and saturated NaCl and dried and concentrated. Chromatography over silica gel (EtOAc/CH2Cl2, 5-10%) gives 18 mg (22%) of N-[4-(3-cyano-1-ethyl-6-hydroxy-1H-indol-2-yl)-phenyl]methanesulfonamide as a tan solid.

Workup

extractionextracted with EtOAc (3×)
washThe combined organic phases are washed with H2O and saturated NaCl
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-2ef5fc2333594833b885bd4baeb71e72
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868037B2

Reaction notes

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