4-(Difluoromethoxy)benzyl Bromide → N-Benzyl-5-(4-(4-(difluoromethoxy)benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

HRID 1887315Notes

Reaction equation

HRID 1887315 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH:10]([F:12])[F:11])=[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]([O:9][CH:10]([F:12])[F:11])=[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 27370014-(Difluoromethoxy)benzyl BromideHCID 54742340N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Product 1

HCID 24983969N-Benzyl-5-(4-(4-(difluoromethoxy)benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamideYield 35%

Procedure

Following the procedure as described in Example 9, making variations only as required to use 1-(bromomethyl)-4-(difluoromethoxy)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 pinkish solid in 35% yield: mp 178-180° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (t, J=6.0 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.53 (d, J=8.5 Hz, 2H) 7.38-7.20 (m, 9H), 6.28 (dd, J=7.9, 2.7 Hz, 1H), 6.14 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.41 (d, J=6.0 Hz, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.1, 162.4, 160.9, 150.8, 139.6, 138.8, 137.2, 135.1, 132.4, 129.9, 128.2, 127.3, 127.4, 127.1, 126.6, 120.6, 118.7, 116.2, 102.5, 97.3, 69.2, 42.5, 15.5; MS (ES+) m/z 497.3 (M+1).

Sources & evidence

ORD record
ord-5e7a225f854d45cd8e79d327bbc81329
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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