3-(benzyloxy)-5-bromo-1-(4-butylphenyl)pyridin-4(1H)-one → 3-(benzyloxy)-1-(4-butylphenyl)-5-cyclopropylpyridin-4(1H)-one

HRID 1056884Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13](Br)=[CH:12][N:11]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[CH:28]1([Zn+])[CH2:30][CH2:29]1>C1COCC1>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:28]2[CH2:30][CH2:29]2)=[CH:12][N:11]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH3:26])=[CH:19][CH:18]=2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(Benzyloxy)-5-bromo-1-(4-butylphenyl)pyridin-4(1H)-one (37 mg, 0.09 mmol) was treated with 1,-bis(diphenylphosphino)ferrocene dichloro palladium(il) dichloromethane complex (6.6 mg, 0.009 mmol) and cyclopropylzinc bromide (0.54 mL of a 0.5 M solution in THF, 0.27 mmol). The reaction vessel was purged with N2, sealed, and heated at 60° C. for 1 h, after which it was concentrated under a stream of N2 and purified by flash chromatography (4 g Si02, 0-55% ethyl acetate/hexanes) to provide 3-(benzyloxy)-1-(4-butylphenyl)-5-cyclopropylpyridin-4(1H)-one. LC/MS (M+H)+ 374.

Workup

customThe reaction vessel was purged with N2
customsealed
concentrationafter which it was concentrated under a stream of N2
custompurified by flash chromatography (4 g Si02, 0-55% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-cb8a2b6483a04fac81947cd71e2d72fb
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399651B2

Reaction notes

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