Allyl bromide → 2-(Acetyl-allyl-amino)-6-chloroisonicotinic acid ethyl ester

HRID 1664218Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([NH:12][C:13](=[O:15])[CH3:14])[CH:6]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[CH:24]=[CH2:25]>CN(C=O)C.O.CC(OC)(C)C>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([Cl:11])[N:8]=[C:7]([N:12]([C:13](=[O:15])[CH3:14])[CH2:25][CH:24]=[CH2:23])[CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6.0 g (25 mmol) 2-acetylamino-6-chloro-isonicotinic acid ethyl ester, 10.36 g (75 mmol) potassium carbonate and 4.23 ml (50 mmol) allyl bromide in 25 ml DMF is stirred at 60° C. for 24 h. The cooled mixture is diluted with water and TBME. The organic phase is washed with water, dried over Na2SO4 and evaporated. The product is purified by chromatography on silica gel (hexane/EtOAc 9/1) to yield the title compound as a yellowish oil.

Workup

washThe organic phase is washed with water
dry with materialdried over Na2SO4
customevaporated
customThe product is purified by chromatography on silica gel (hexane/EtOAc 9/1)

Sources & evidence

ORD record: ord-84562b72ef1d4f4d813faf0271d36dbf
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039455B2

Reaction notes

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