2-(Bromomethyl)-3-chloro-1,4-difluorobenzene → 1-(2-Chloro-3,6-difluorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 659317Notes

Reaction equation

HRID 659317 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.[Cl:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([F:23])[C:15]=1[CH2:16]Br>>[Cl:13][C:14]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]([F:23])[C:15]=1[CH2:16][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 27735492-(Bromomethyl)-3-chloro-1,4-difluorobenzeneHCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 578858011-(2-Chloro-3,6-difluorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Procedure

7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (300 mg) was reacted with 2-chloro-3,6-difluorobenzyl bromide as in General Procedure 1. The title compound was obtained as an off white solid (63% yield). M.p. 237° C., LCMS: m/z=436.17 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 4.01 (s, 2H), 5.24 (s, 2H), 7.05 (d, J=1.5 Hz, 1H), 7.23-7.32 (m, 1H), 7.41-7.48 (m, 1H), 7.79 (d, J=1.5 Hz, 1H).

Sources & evidence

ORD record
ord-c20e90ca408949d6aeb688dc6c647e6f
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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