Boron tribromide → HCID 23725202, compound

HRID 2219411Notes

Reaction equation

[C:1]1([C:7]2[C:11]([C:12]3[N:13]=[CH:14][N:15]([C:17]4[CH:22]=[CH:21][C:20](C(=O)C)=[CH:19][CH:18]=4)[CH:16]=3)=[C:10]([CH2:26][O:27]C)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[C:1]1([C:7]2[C:11]([C:12]3[N:13]=[CH:14][N:15]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:16]=3)=[C:10]([CH2:26][OH:27])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 1-(4-{4-[3-phenyl-5-methoxymethyl-isoxazol-4-yl]-imidazol-1-yl}-phenyl)-ethanone (147 mg, 0.44 mmol) in dry dichloromethane (4 mL) was added slowly boron tribromide (334 mg, 1.33 mmol) at dry ice-acetone bath cooling temperature. After complete addition, the resulting mixture was stirred at −78° C. for 15 min, and then allowed to warm up to room temperature for 35 min. The reaction was quenched with saturated sodium bicarbonate. The organic layer was separated, and the aqueous phase was extracted with dichloromethane and ethylacetate. The combined organic solution was dried over sodium sulphate and evaporated. Purification by preparative HPLC afforded the title compound (98 mg, 70%) which was obtained as an off-white solid. MS: m/e=318.0 [M+H]+.

Workup

temperaturecooling temperature
additionAfter complete addition
temperatureto warm up to room temperature for 35 min
customThe reaction was quenched with saturated sodium bicarbonate
customThe organic layer was separated
extractionthe aqueous phase was extracted with dichloromethane and ethylacetate
dry with materialThe combined organic solution was dried over sodium sulphate
customevaporated
customPurification by preparative HPLC

Sources & evidence

ORD record: ord-48a692444ad545ffbb11f1d1685c3eb1
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414061B2

Reaction notes

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