5-Fluoro-2-(trifluoromethyl)benzyl bromide → 1-(5-Fluoro-2-trifluoromethylbenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 659402Notes

Reaction equation

HRID 659402 reaction equation
[I:1][C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:22]([F:25])([F:24])[F:23])=[C:18]([CH:21]=1)[CH2:19]Br>>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:22]([F:23])([F:24])[F:25])=[C:18]([CH:21]=1)[CH2:19][N:9]1[C:8](=[O:10])[CH2:7][NH:6][C:5]2[N:11]=[CH:12][C:2]([I:1])=[CH:3][C:4]1=2

Participants

3

Reactant 2

HCID 27375785-Fluoro-2-(trifluoromethyl)benzyl bromideHCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 578858801-(5-Fluoro-2-trifluoromethylbenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 51%

Procedure

7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (1.07 g) was reacted with 5-fluoro-2-trifluoromethylbenzyl bromide as in General Procedure 1 to give the title compound as an off-white solid (51% yield). M.p. 244-245° C., LCMS: m/z=453.03 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 4.21 (s, 2H), 5.15 (s, 2H), 6.97 (s, 1H0, 7.12 (d, J=9.8 Hz, 1H), 7.25 (s, 1H), 7.36 (dd, J=8.3 Hz, 1H), 7.84 (s, 1H), 7.88-7.94 (m, 1H).

Sources & evidence

ORD record
ord-8011bd0f352245789b6e3ba0cd7183ef
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

Loading…