Water → 4-{6-Amino-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}thiophene-2-carboxylic Acid

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Reaction Conditions

Reaction Steps

3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine (180.0 mg, 0.4285 mmol), 2-carboxythiophene-4-boronic acid (147 mg, 0.857 mmol), potassium carbonate (178 mg, 1.28 mmol), 1,4-dioxane (4.2 mL, 54 mmol), H2O (1.2 mL, 67 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (20 mg, 0.02 mmol) were mixed and heated in a microwave reactor at 90° C. for 20 minutes. The crude was passed through Thiol-SPE to remove palladium. MS (ES+): m/z 467.02/469.02 (100/70) [MH+]. HPLC: tR=0.85 min (HPLC-ACQUITY, Analytical). 1H NMR (400 MHz, DMSO-d6): δ=1.84 (d, J=6.8 Hz, 3H), 5.63 (s, 2H), 6.26 (q, J=6.8 Hz, 1H), 7.45 (t, J=8.7 Hz, 1H), 7.53 (dd, J=9.0, 4.9 Hz, 1H), 7.76 (br. s., 1H), 7.94 (br. s., 1H), 8.20 (s, 1H), 8.40 (s, 1H).

Provenance & Evidence