1-(Bromomethyl)-4-(trifluoromethyl)benzene → ethyl 4-methyl-2-(5-oxo-1-((5-(trifluoromethyl)furan-2-yl)methyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

HRID 2067515Notes

Reaction equation

HRID 2067515 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][C:15]1[O:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1.[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[C:39](=[O:40])[NH:38][N:37]=[CH:36]2)[S:28][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH3:24][C:25]1[N:26]=[C:27]([N:35]2[C:39](=[O:40])[N:38]([CH2:14][C:15]3[O:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=3)[N:37]=[CH:36]2)[S:28][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 58031650ethyl 4-methyl-2-(5-oxo-1-((5-(trifluoromethyl)furan-2-yl)methyl)-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylateYield 56%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 2-(bromomethyl)-5-(trifluoromethyl)furan to react with ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate, the title compound was obtained as a white solid in 56% yield: 1H NMR (300 MHz, CDCl3) δ 8.26 (s, 1H), 6.69-6.62 (m, 1H), 6.29-6.20 (m, 1H), 5.03 (s, 2H), 4.32 (q, J=7.0 Hz, 2H), 2.64 (s, 3H), 1.35 (t, J=7.0 Hz, 3H); MS (ES+) m/z 403.3 (M+1).

Sources & evidence

ORD record
ord-f647a255566b4d34838f1af3412119bc
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

Loading…