1-(Bromomethyl)-4-(trifluoromethyl)benzene → ethyl 2-(1-(2-(4-fluorophenoxy)ethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylate

HRID 2067520Notes

Reaction equation

HRID 2067520 reaction equation
FC(F)(F)C1C=CC(CBr)=CC=1.Br[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=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]>>[F:23][C:20]1[CH:21]=[CH:22][C:17]([O:16][CH2:15][CH2:14][N:38]2[C:39](=[O:40])[N:35]([C:27]3[S:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:25]([CH3:24])[N:26]=3)[CH:36]=[N:37]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 20641711-(2-Bromoethoxy)-4-fluorobenzeneHCID 57920013ethyl 4-methyl-2-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiazole-5-carboxylate

Product 1

HCID 58031498ethyl 2-(1-(2-(4-fluorophenoxy)ethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-4-methylthiazole-5-carboxylateYield 48%

Procedure

Following the procedure as described in Example 19, making variation as required to replace 4-(trifluoromethyl)benzyl bromide with 1-(2-bromoethoxy)-4-fluorobenzene 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 48% yield: 1H NMR (300 MHz, CDCl3) δ 8.26 (s, 1H), 6.93-6.84 (m, 2H), 6.81-6.75 (m, 2H), 4.32-4.15 (m, 6H), 2.62 (s, 3H), 1.31 (t, J=7.1 Hz, 3H); MS (ES+) m/z 393.3 (M+1).

Sources & evidence

ORD record
ord-eea632aab676469a886ba9dcddae0a9d
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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