Phosphorus tribromide → 5-(Bromomethyl)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine

HRID 709811Notes

Reaction equation

P(Br)(Br)[Br:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[C:14]1[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][C:15]=1[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].C(=O)([O-])O.[Na+]>CN(C=O)C>[Br:2][CH2:20][C:17]1[CH:16]=[C:15]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:14]([C:7]2[CH:8]=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:6]=2[F:5])=[N:19][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, phosphorus tribromide (37 μL) was added to DMF (1.0 mL) at 0° C. and the mixture was stirred at 0° C. for 5 min. To the obtained white suspension was added (6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methanol (100 mg), and the mixture was stirred at room temperature for 30 min. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound (88 mg) as a pale-yellow oil. This compound was used for the next step without further purification.

Workup

stirringthe mixture was stirred at room temperature for 30 min
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-82ee5dd5c2eb4810bf6799a2725434c4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181186B2

Reaction notes

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