Sodium Carbonate → HCID 86696582, compound

HRID 1854871Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:18])=[C:11](Cl)[CH:12]=[CH:13]2)=[C:8]([CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)=[O:5])[CH3:2].[OH:22][C:23]1[CH:28]=[CH:27][C:26](B(O)OC)=[CH:25][CH:24]=1.[C:33]([O-])([O-])=O.[Na+].[Na+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:18])=[C:11]([C:26]3[CH:27]=[CH:28][C:23]([OH:22])=[CH:24][C:25]=3[CH3:33])[CH:12]=[CH:13]2)=[C:8]([CH:19]2[CH2:21][CH2:20]2)[CH:7]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester (120 mg, 0.400 mmol), 4-hydroxy-methyl-phenyl boronic acid (73 mg, 0.48 mmol), (Ph3P)2PdCl2 (28 mg, 0.040 mmol), and Na2CO3 (190 mg in 0.8 mL of water, 1.80 mmol) in THF (5 mL) was degassed 3 times under N2 and heated to 80° C. overnight. The reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (2×20 mL). The organic phase was separated, dried, and concentrated. The residue was purified by flash silica column chromatography (hexane:ethyl acetate, 1:3 to pure ethyl acetate) to afford the title compound as a yellow solid (60 mg, 40%). ESI-MS m/z: 378 (M+H)+.

Workup

customwas degassed 3 times under N2
additionThe reaction mixture was diluted with ethyl acetate (50 mL)
washwashed with water (2×20 mL)
customThe organic phase was separated
customdried
concentrationconcentrated
customThe residue was purified by flash silica column chromatography (hexane:ethyl acetate, 1:3 to pure ethyl acetate)

Sources & evidence

ORD record: ord-84ed7dbc9c8e4e228465df0b734aeb03
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962842B2

Reaction notes

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