Boron tribromide → 4-[6-(2-Fluorophenoxy)oxazolo[4,5-c]pyridin-2-yl]-2,6-dimethylphenol

HRID 1401112Notes

Reaction equation

[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]2[N:11]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([O:21]C)=[C:16]([CH3:23])[CH:15]=3)[O:13][C:7]=2[CH:6]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:10]=[CH:9][C:8]2[N:11]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:23])[C:17]([OH:21])=[C:18]([CH3:20])[CH:19]=3)[O:13][C:7]=2[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 60 mg of 6-(2-fluorophenoxy)-2-(4-methoxy-3,5-dimethylphenyl)oxazolo[4,5-c]pyridine in 2 ml of dichloromethane was cooled to 0° C., and 0.4 ml of a 1 M solution of boron tribromide in dichloromethane were added over a period of 10 min. The mixture was stirred at 0° C. for 1 h and a further 0.2 ml of a 1 M solution of boron tribromide in dichloromethane was then added. The reaction was then stirred at room temperature for 16 h. For work-up, saturated aqueous sodium bicarbonate solution was added slowly to the reaction mixture. The precipitate was filtered off, washed with water and dried under reduced pressure. This gave 41 mg (71%) of the title compound.

Workup

stirringThe reaction was then stirred at room temperature for 16 h
filtrationThe precipitate was filtered off
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-b2ce144e71494aa0a032b19947bb3658
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907093B2

Reaction notes

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