4-Ethoxycarbonylphenylboronic acid → HCID 57885995, compound

HRID 1819131Notes

Reaction equation

I[C:2]1[CH:23]=[N:22][C:5]2[NH:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][C:18]([F:21])([F:20])[F:19])[C:4]=2[CH:3]=1.[CH2:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28])[CH3:25]>>[CH2:24]([O:26][C:27](=[O:28])[C:29]1[CH:34]=[CH:33][C:32]([C:2]2[CH:23]=[N:22][C:5]3[NH:6][CH2:7][CH2:8][N:9]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[O:17][C:18]([F:21])([F:20])[F:19])[C:4]=3[CH:3]=2)=[CH:31][CH:30]=1)[CH3:25]

Participants

Reactant 2

HCID 27343504-Ethoxycarbonylphenylboronic acid

HCID 57886101HCID 57886101, compound

Product 1

HCID 57885995HCID 57885995, compound

Procedure

7-Iodo-1-[2-(trifluoromethoxy)benzyl]-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine (699 mg) was reacted with (4-ethoxycarbonylphenyl)boronic acid as in General Procedure 4B to give the title compound as a yellow solid. m.p.=153° C., LCMS: m/z=458.00 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.38 (3H, t, J=7.1 Hz), 3.47 (2H, m), 3.64 (2H, m), 4.36 (2H, quartet, J=7.1 Hz), 4.56 (2H, s), 5.22 (1H, bs), 6.73 (1H, s), 7.25 (1H, m), 7.31 (2H, m), 7.37 (1H, d, J=7.3 Hz), 7.42 (2H, d, J=7.8. Hz), 7.75 (1H, s), 8.00 (2H, d, J=8.1 Hz).

Sources & evidence

ORD record: ord-2411007c2bf84a188d34b59c5d181256
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601716B2

Reaction notes

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