1-(Bromomethyl)-4-(trifluoromethyl)benzene → N-Benzyl-3-methyl-5-(2-oxo-4-(4-(trifluoromethyl)benzyloxy)pyridin-1(2H)-yl)thiophene-2-carboxamide

HRID 1887313Notes

Reaction equation

HRID 1887313 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[CH2:13]([NH:20][C:21]([C:23]1[S:24][C:25]([N:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]2=[O:36])=[CH:26][C:27]=1[CH3:28])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH2:13]([NH:20][C:21]([C:23]1[S:24][C:25]([N:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:2][C:3]3[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=3)=[CH:31][C:30]2=[O:36])=[CH:26][C:27]=1[CH3:28])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 54742340N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Product 1

HCID 24983816N-Benzyl-3-methyl-5-(2-oxo-4-(4-(trifluoromethyl)benzyloxy)pyridin-1(2H)-yl)thiophene-2-carboxamideYield 42%

Procedure

Following the procedure as described in Example 9, making variations only as required to use 1-(bromomethyl)-4-(trifluoromethyl)benzene in place of 2-cyclopropylethyl 4-methylbenzenesulfonate to react with N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide, the title compound was obtained as a colorless solid in 42% yield: mp 225-227° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.56 (t, J=6.0 Hz, 1H), 8.18 (d, J=7.9 Hz, 1H), 7.80 (d, J=8.2 Hz, 2H), 7.68 (d, J=8.1 Hz, 2H), 7.37-7.20 (m, 6H), 6.32 (dd, J=7.9, 2.8 Hz, 1H), 6.14 (d, J=2.8 Hz, 1H), 5.30 (s, 2H), 4.41 (d, J=6.0 Hz, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.0, 162.4, 160.9, 140.3, 139.6, 138.7, 137.2, 135.2, 128.2 (d, JC-F=3.7 Hz), 127.4, 127.1, 126.6, 125.4 (d, JC-F=3.8 Hz), 120.7, 102.4, 97.5, 69.0, 42.5, 15.5; MS (ES+) m/z 499.3 (M+1).

Sources & evidence

ORD record
ord-c1d669c2070b4d04895fc3d6ef4f68ad
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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