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

HRID 659403Notes

Reaction equation

HRID 659403 reaction equation
I[C:2]1[CH:12]=[N:11][C:5]2[NH:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[CH2:13]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17])[CH3:14]>>[CH2:13]([O:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:12]=[N:11][C:5]3[NH:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=3[CH:3]=2)=[CH:20][CH:19]=1)[CH3:14]

Participants

3

Reactant 2

HCID 27343504-Ethoxycarbonylphenylboronic acidHCID 448291147-iodo-3,4-dihydropyrido[2,3-b]pyrazin-2(1H)-one

Product 1

HCID 578858884-(2-Oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)benzoic acid ethyl esterYield 79%

Procedure

7-Iodo-3,4-dihydro-1H-pyrido[2,3-b]pyrazin-2-one (520 mg) was reacted with 4-ethoxycarbonylphenyl boronic acid as in General Procedure 4B to give the title compound as a light yellow solid in 79% yield. M.p.>200° C., LCMS: m/z=298.14 (M+H+), 1H-NMR (DMSO-d6, 400 MHz) δ 1.33 (3H, t, J=7.1 Hz), 4.32 (2H, q, J=7.1 Hz), 7.26 (1H, d, J=2.0 Hz), 7.67 (2H, d, J=8.3 Hz), 7.99 (2H, d, J=8.1 Hz), 8.04 (1H, d, J=2.3 Hz).

Sources & evidence

ORD record
ord-77ce78a734544c0c9fb81cec09f46981
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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