2-(Bromomethyl)-1,4-difluorobenzene → 1-(2,5-Difluorobenzyl)-7-iodo-3,3-dimethyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 659370Notes

Reaction equation

HRID 659370 reaction equation
[I:1][C:2]1[CH:14]=[N:13][C:5]2[NH:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[F:15][C:16]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:17]=1[CH2:18]Br>>[F:15][C:16]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:17]=1[CH2:18][N:9]1[C:8](=[O:10])[C:7]([CH3:11])([CH3:12])[NH:6][C:5]2[N:13]=[CH:14][C:2]([I:1])=[CH:3][C:4]1=2

Participants

3

Reactant 2

HCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 578860407-iodo-3,3-dimethyl-1H,2H,3H,4H-pyrido[2,3-b]pyrazin-2-one

Product 1

HCID 578858051-(2,5-Difluorobenzyl)-7-iodo-3,3-dimethyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 98%

Procedure

7-Iodo-3,3-dimethyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (237 mg) was reacted with 2,5-difluorobenzyl bromide as in General Procedure 1 to give the title compound as a white solid (98% yield). M.p. 198-201° C., LCMS: m/z=430.00 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.36 (s, 6H), 5.12 (s, 2H), 6.79-6.83 (m, 1H), 7.15-7.22 (m, 1H), 7.28-7.32 (m, 1H), 7.31 (s, 1H), 7.40 (s, 1H), 7.90 (s, 1H).

Sources & evidence

ORD record
ord-7a99b6920c4b4af19e0bbf306cfd5154
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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