4-(Methanesulfonyl)phenylboronic acid → 1-Benzyl-7-(4-methanesulfonyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 2074548Notes

Reaction equation

HRID 2074548 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][NH:11][C:10]2[N:15]=[CH:16][C:17](I)=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22]>>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][NH:11][C:10]2[N:15]=[CH:16][C:17]([C:27]3[CH:28]=[CH:29][C:24]([S:21]([CH3:20])(=[O:23])=[O:22])=[CH:25][CH:26]=3)=[CH:18][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 578859791-Benzyl-7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 248525711-Benzyl-7-(4-methanesulfonyl-phenyl)-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 43%

Procedure

1-Benzyl-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (46 mg) was reacted with 4-(methanesulfonyl)phenyl boronic acid as in General Procedure 4B to give the title compound as a yellow solid (43% yield). LCMS: m/z=394.22 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.08 (3H, s), 4.54 (2H, s), 5.28 (2H, s), 7.30 (3H, m), 7.39 (3H, m), 7.45 (2H, d, J=8.3 Hz), 7.78 (1H, d, J=1.5 Hz), 7.94 (2H, d, J=8.3 Hz).

Sources & evidence

ORD record
ord-7abe846ccd134f3997adad06bc565f78
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

Loading…