4-Fluorobenzyl bromide → N-Benzyl-5-(4-(4-fluorobenzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

HRID 1887314Notes

Reaction equation

HRID 1887314 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH2:10]([NH:17][C:18]([C:20]1[S:21][C:22]([N:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][C:27]2=[O:33])=[CH:23][C:24]=1[CH3:25])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:18]([C:20]1[S:21][C:22]([N:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:2][C:3]3[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=3)=[CH:28][C:27]2=[O:33])=[CH:23][C:24]=1[CH3:25])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 54742340N-benzyl-5-(4-hydroxy-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamide

Product 1

HCID 24983817N-Benzyl-5-(4-(4-fluorobenzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxamideYield 43%

Procedure

Following the procedure as described in Example 9, making variations only as required to use 1-(bromomethyl)-4-fluorobenzene 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 pale yellow solid in 43% yield: mp 195-197° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.56 (t, J=6.0 Hz, 1H), 8.16 (d, J=8.0 Hz, 1H), 7.55-7.49 (m, 2H), 7.37-7.20 (m, 8H), 6.28 (dd, J=7.9, 2.7 Hz, 1H), 6.15 (d, J=2.7 Hz, 1H), 5.14 (s, 2H), 4.41 (d, J=6.0 Hz, 2H), 2.42 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 162.4, 160.9, 139.6, 138.8, 137.2, 135.2, 135.1, 131.7 (d, JC-F=3.0 Hz), 130.4 (d, JC-F=8.4 Hz), 128.2, 127.3, 127.1, 126.6, 120.6, 115.3 (d, JC-F=21.5 Hz), 102.5, 97.3, 69.3, 42.5, 15.5; MS (ES+) m/z 449.3 (M+1).

Sources & evidence

ORD record
ord-605b1d97ad0b4fab84e8d8f600d163b9
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

Loading…