(3-Chlorophenyl)boronic acid → isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

HRID 1007115Notes

Reaction equation

HRID 1007115 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([NH:6][C:7](=[O:18])[CH2:8][N:9]2[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1>>[Cl:19][C:20]1[CH:25]=[C:24]([C:2]2[CH:11]=[C:10]3[C:5]([NH:6][C:7](=[O:18])[CH2:8][N:9]3[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:4][CH:3]=2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 2734323(3-Chlorophenyl)boronic acidHCID 18464405isopropyl 7-bromo-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

Product 1

HCID 22667742isopropyl 7-(3-chlorophenyl)-3-oxo-3,4-dihydroquinoxaline-1(2H)-carboxylate

Procedure

The title compound was prepared according to the procedure for Example 5 from isopropyl 7-bromo-3-oxo-3,4-dihydroquinoxaline-1 (2H)-carboxylate (6.3 g, 20 mmol), and 3-chlorophenyl boronic acid (3.2 g, 20 mmol). Off-white crystals (3.7 g, 49%): m.p. 174-176° C. 1H-NMR (DMSO-d6) δ 1.27 (d, J=6.4 Hz, 6H), 4.30 (s, 2H), 4.94 (sep, J=6.2 Hz, 1H), 7.04 (d, J=8.3 Hz, 1H), 7.50 (m, 4H), 7.61 (t, J=1.9 Hz, 1H), 7.86 (s, 1H), 10.79 (s, 1H), MS(APCI) m/z 345/347 (M+H)+.

Sources & evidence

ORD record
ord-7bc9c524f5fb40f18eb2676da623f235
Source dataset
uspto-grants-2004_09
Patent number
US06794373B2

Reaction notes

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