4-Ethoxycarbonylphenylboronic acid → 4-[1-(2,6-Dichlorobenzyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid ethyl ester
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.[CH2:22]([O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)=[O:26])[CH3:23]>>[CH2:22]([O:24][C:25](=[O:26])[C:27]1[CH:32]=[CH:31][C:30]([C:14]2[CH:13]=[N:12][C:7]3[NH:8][CH2:9][C:10](=[O:11])[N:5]([CH2:4][C:3]4[C:2]([Cl:1])=[CH:20][CH:19]=[CH:18][C:17]=4[Cl:21])[C:6]=3[CH:15]=2)=[CH:29][CH:28]=1)[CH3:23]Participants
3
Procedure
1-(2,6-Dichlorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (231 mg) was reacted with 4-ethoxycarbonyl phenyl boronic acid as in General Procedure 4B to give the title compound as a yellow solid. M.p.=226° C., LCMS: m/z=456.52 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.35 (3H, t, J=6.9 Hz), 4.09 (3H, s), 4.33 (3H, q, J=7.1 Hz), 5.47 (2H, s), 7.32 (2H, m), 7.48 (2H, d, J=8.1 Hz), 7.57 (3H, m), 7.63 (1H, m), 7.90 (1H, m), 7.98 (2H, d, J=8.2 Hz), 8.03 (1H, d, J=2.0 Hz).
Sources & evidence
- ORD record
- ord-62ac1962d7f74d719f84bfa385a14183
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080561B2
Reaction notes
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