Sodium Carbonate → 8-Chloro-2-phenylquinoline-3-carbaldehyde

HRID 572124Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([Cl:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>COCCOC>[Cl:14][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:11]([CH:12]=[O:13])=[CH:10]2

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2,8-dichloroquinoline-3-carbaldehyde (2.0 g, 8.85 mmol), 2M aqueous Na2CO3 solution (8 mL), phenylboronic acid (1.5 g, 12.3 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.25 g, 0.216 mmol) in DME (30 mL) was degassed and the mixture heated at 110° C. for 4 h. The mixture was allowed to cool to room temperature, diluted with EtOAc and washed with brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The resultant solid was triturated in ether, filtered, washed with small amount of ether, then light petroleum, and dried, to give the title compound (2.3 g, 97%) as an off-white solid. δH (CDCl3) 10.25 (s, 1H), 8.86 (s, 1H), 7.95-8.02 (m, 2H), 7.78-7.14 (m, 2H), 7.54-7.62 (m, 4H). LCMS (ES+) 268 (M+H)+, RT 1.98 minutes.

Workup

customwas degassed
temperatureto cool to room temperature
additiondiluted with EtOAc
washwashed with brine
dry with materialThe organic layer was dried (MgSO4)
customthe solvent was removed under reduced pressure
customThe resultant solid was triturated in ether
filtrationfiltered
washwashed with small amount of ether
dry with materiallight petroleum, and dried

Sources & evidence

ORD record: ord-1067cffe72574f88a3bfb8c2126e43b4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029392B2

Reaction notes

Loading…