Potassium Carbonate → Methyl 3-{[[(6-fluoro-3'-formyl-3-biphenylyl)methyl](methyl)amino]carbonyl}benzoate

HRID 564528Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:9][N:10]([CH3:23])[C:11]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:12])[CH:5]=[CH:6][C:7]=1[F:8].[CH:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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>[F:8][C:7]1[C:2]([C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([CH:24]=[O:25])[CH:27]=2)=[CH:3][C:4]([CH2:9][N:10]([CH3:23])[C:11]([C:13]2[CH:14]=[C:15]([CH:20]=[CH:21][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:12])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of methyl 3-{[[(3-bromo-4-fluorophenyl)methyl]-(methyl)amino]carbonyl}benzoate (0.20 g, 0.526 mmol) in p-dioxane/H2O (4.5/1.5 mL) was added (4-formylphenyl)boronic acid (0.118 g, 0.789 mmol), Pd(PPh3)4 (0.030 g, 0.026 mmol), and K2CO3 (0.29 mL, 2.1 mmol). The mixture was heated in a microwave at 130° C. for 15 min. It was then filtered, concentrated and the concentrate purified by CombiFlash chromatograph to afford the title compound 0.184 g (86%). LC-MS m/z 406 (M+H)+.

Workup

filtrationIt was then filtered
concentrationconcentrated
customthe concentrate purified by CombiFlash chromatograph

Sources & evidence

ORD record: ord-58c4672023064a0b96d44e845f62f1c4
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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