Boron tribromide → HCID 22627290, compound

HRID 278125Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:16])=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH2:18][O:19]C)=[C:6]1[CH2:22][CH2:23][CH3:24].B(Br)(Br)Br>ClCCl.CO.O>[Cl:1][C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([NH2:16])=[O:15])[CH:12]=2)[C:7]([C:17](=[O:21])[CH2:18][OH:19])=[C:6]1[CH2:22][CH2:23][CH3:24]

Participants

Conditions

Temperature: -12 °C

Procedure

To a solution of 1-(2-chlorobenzyl)-3-methoxyacetyl-2-propylindole-6-carboxamide (168 mg) in a mixture of dichloromethane (10 ml) and methanol (0.5 ml) was added 1M solution of boron tribromide in dichloromethane (2.5 ml) at −53° C. The reaction mixture was warmed gradually to −12° C. during 3 hours. Then 1M solution of boron tribromide in dichloromethane (2.5 ml) was added, and the mixture was stirred for 20 minutes at −12° C. The reaction mixture was diluted with water and extracted with 10% methanol in chloroform. The organic phase was washed with aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl acetate and washed with hexane to give 1-(2-chlorobenzyl)-3-hydroxyacetyl-2-propylindole-6-carboxamide (120 mg) as colorless crystals.

Workup

extractionextracted with 10% methanol in chloroform
washThe organic phase was washed with aqueous sodium bicarbonate, water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was crystallized from ethyl acetate
washwashed with hexane

Sources & evidence

ORD record: ord-7ac6e520b480482c86bc1b855a90ed9e
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06358992B1

Reaction notes

Loading…