3-Pyridinylboronic acid → 1-(2,6-Dichlorobenzyl)-7-pyridin-3-yl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 659405Notes

Reaction equation

HRID 659405 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH2:9][NH:8][C:7]2[N:12]=[CH:13][C:14](I)=[CH:15][C:6]1=2.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24](B(O)O)[CH:23]=1>>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[CH2:9][NH:8][C:7]2[N:12]=[CH:13][C:14]([C:24]3[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=3)=[CH:15][C:6]1=2

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 578858121-(2,6-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Product 1

HCID 578859051-(2,6-Dichlorobenzyl)-7-pyridin-3-yl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Procedure

1-(2,6-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (150 mg) was reacted with pyridine-3-boronic acid as in General Procedure 4B to give the title compound as a brown solid. M.p.>200° C., LCMS: m/z=385.48 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 4.06 (2H, s), 5.45 (2H, s), 7.07 (1H, s), 7.45 (5H, m), 7.85 (1H, d, J=7.8 Hz), 8.01 (1H, s), 8.49 (1H, d, J=4.8 Hz), 8.67 (1H, s) (NMR and LCMS indicate presence of triphenylphosphine impurity)

Sources & evidence

ORD record
ord-b3b6e2642bea416cae040369c116a9c6
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

Loading…