Ethyl 2-carbamothioylnicotinate → Ethyl 2-(4-(4-fluorophenyl)thiazol-2-yl)nicotinate

HRID 1400223Notes

Reaction equation

HRID 1400223 reaction equation
[C:1]([C:4]1[N:14]=[CH:13][CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[S:3])[NH2:2].CN(C=O)C.[F:20][C:21]1[CH:30]=[CH:29][C:24]([C:25](=O)[CH2:26]Br)=[CH:23][CH:22]=1>>[F:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]2[N:2]=[C:1]([C:4]3[N:14]=[CH:13][CH:12]=[CH:11][C:5]=3[C:6]([O:8][CH2:9][CH3:10])=[O:7])[S:3][CH:26]=2)=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 86644784Ethyl 2-carbamothioylnicotinateHCID 86644785DMF 4-fluorophenacylbromide

Product 1

HCID 67540603Ethyl 2-(4-(4-fluorophenyl)thiazol-2-yl)nicotinateYield 14.6%

Procedure

To a suspension of ethyl 2-carbamothioylnicotinate (1.9 g, 9.04 mmol) in 20 ml of DMF 4-fluorophenacylbromide (2.0 g, 9.22 mmol) was added, and the resulting mixture stirred for 2 hours at room temperature. The mixture was filtered under suction, the mother liquor evaporated to dryness, and the remaining oil purified by chromatography on silica gel (eluent: CH2Cl2+0-5% methanol) to give 434 mg of the title compound as amorphous solid.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered under suction
  3. customthe mother liquor evaporated to dryness
  4. customthe remaining oil purified by chromatography on silica gel (eluent: CH2Cl2+0-5% methanol)

Sources & evidence

ORD record
ord-bb3b53edfa434262a96cc53f224d799c
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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