4-Ethoxycarbonylphenylboronic acid → 4-[1-(2,5-Difluorobenzyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid ethyl ester

HRID 1818999Notes

Reaction equation

HRID 1818999 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][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[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:2]=4[F:1])[C:6]=3[CH:15]=2)=[CH:29][CH:28]=1)[CH3:23]

Participants

3

Reactant 2

HCID 27343504-Ethoxycarbonylphenylboronic acidHCID 670918851-(2,5-Difluorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

Product 1

HCID 248530164-[1-(2,5-Difluorobenzyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]benzoic acid ethyl esterYield 62%

Procedure

1-(2,5-Difluorobenzyl)-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (600 mg) was reacted with 4-ethoxycarbonyl phenyl boronic acid as in General Procedure 4A to give the title compound as an off-white solid (62% yield). M.p. 201-203° C., LCMS: m/z=424.20 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.32 (t, J=7.0 Hz, 3H), 3.99 (s, 2H), 4.32 (q, J=7.0 Hz, 2H), 5.26 (s, 2H), 7.03-7.09 (m, 1H), 7.11-7.19 (m, 1H), 7.33 (s, 1H), 7.34-7.38 (m, 1H), 7.39 (s, 1H), 7.67 (d, J=7.0 Hz, 2H), 6.8 Hz, 2H), 8.10 (s, 1H).

Sources & evidence

ORD record
ord-1cb43a1371944663926ea272de3e279c
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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