4-Acetylphenylboronic acid → 7-(4-Acetylphenyl)-1-benzyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one

HRID 1818979Notes

Reaction equation

HRID 1818979 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.[C:20]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)(=[O:22])[CH3:21]>>[C:20]([C:23]1[CH:28]=[CH:27][C:26]([C:17]2[CH:16]=[N:15][C:10]3[NH:11][CH2:12][C:13](=[O:14])[N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:9]=3[CH:18]=2)=[CH:25][CH:24]=1)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 37021224-Acetylphenylboronic acidHCID 578859791-Benzyl-7-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 248524657-(4-Acetylphenyl)-1-benzyl-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-oneYield 20%

Procedure

1-Benzyl-7-iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (35 mg) was reacted with 4-acetylphenyl boronic acid as in General Procedure 4B to give the title compound as a yellow solid (20% yield). M.p.=200° C., LCMS: m/z=358.24 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.61 (3H, s), 4.36 (2H, s), 5.22 (2H, s), 7.21 (1H, d, J=2.0 Hz), 7.28 (4H, m), 7.37 (4H, m), 7.96 (2H, d, J=8.3 Hz), 8.01 (1H, d, J=1.8 Hz).

Sources & evidence

ORD record
ord-a53bdf63b62844a58e5e1c77635fb2dd
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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