2-Bromo-1,2-diphenylethan-1-one → 5-Fluoro-1-(2-oxo-1,2-diphenylethyl)pyridin-2(1H)-one

HRID 1666558Notes

Reaction equation

Br[CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[F:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[N:22][CH:23]=1>C(OCC)(=O)C>[F:17][C:18]1[CH:19]=[CH:20][C:21](=[O:24])[N:22]([CH:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3](=[O:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1.2 g (4.36 mmol) of 2-bromo-1,2-diphenylethanone and 740 mg (6.54 mmol) of 5-fluoro-2-hydroxypyridine were intimately ground in a mortar, and the mixture was subsequently heated at 120° C. for 2 hours. The still hot, oily mass was dissolved in ethyl acetate. Cooling resulted in the 5-fluoro-1-(2-oxo-1,2-diphenylethyl)-1H-pyridin-2-one in crystalline form, 1.01 g (75%), which was immediately dissolved in 15 ml of methanol. After addition of 340 mg (9.03 mmol) of sodium borohydride, the mixture was left at room temperature for one hour and then diluted with water. The resulting mass of crystals was filtered off with suction. The product contains the diastereoisomeric pyrid-2-one alcohols in the ratio of about 1:2 and was not fractionated further.

Workup

temperatureCooling

Sources & evidence

ORD record: ord-cad3e0a229a643a88352f606086caf8b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044074B2

Reaction notes

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