Potassium Carbonate → [5-(4-Fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

HRID 554636Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10](Br)[CH:11]=1)[CH3:2].[F:14][C:15]1[CH:16]=[CH:17][C:18](B2OC(C)(C)C(C)(C)O2)=[C:19]([CH:22]=1)[CH:20]=[O:21].C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:18]2[CH:17]=[CH:16][C:15]([F:14])=[CH:22][C:19]=2[CH:20]=[O:21])[CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 75 °C

Procedure

(5-Bromo-pyridin-3-yl)-acetic acid ethyl ester (1.91 g, 7.8 mmol), 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (50% pure; 2.94 g, 11.75 mmol), and potassium carbonate (3.25 g, 23.5 mmol) were combined in 2:1 DME:H2O, and the solution was purged with N2 for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.45 g, 0.39 mmol) was added, and the reaction was purged with N2 for another 25 minutes and then stirred at 75° C. for 2 hours. The mixture was worked up with EtOAc and H2O, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give [5-(4-fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester.

Workup

customH2O, and the solution was purged with N2 for 20 minutes
customthe reaction was purged with N2 for another 25 minutes
customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-41f391aefce24c35ba710f90ff5ed887
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049015B2

Reaction notes

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