Sodium Bicarbonate → HCID 58293777, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (Compound 1106, 200 mg, 0.4649 mmol) and tert-butyl 4-(5-bromo-3-methylthiophen-2-yl)piperidine-1-carboxylate (Compound 1054, 167.5 mg, 0.4650 mmol) in DMF (8 mL) was added a solution of NaHCO3 (2.509 g, 1.162 mL of 1.2 M, 1.395 mmol). The mixture was degassed under a nitrogen stream for 20 minutes. PdCl2(dppf) (34.02 mg, 0.04650 mmol) was added and the reaction was stirred for 10 minutes at 120° C. under microwave irradiation. The mixture was diluted with EtOAc, filtered, and the filtrate was washed with water. The organics were dried over magnesium sulfate, concentrated, and the resulting residue purified via silica gel chromatography to give tert-butyl 4-(5-(6-amino-5-(1-(2,3-difluoro-4-methoxyphenyl)-1H-tetrazol-5-yl)pyridin-3-yl)-3-methylthiophen-2-yl)piperidine-1-carboxylate (Compound 1107, 230 mg, 83%) as a yellow solid.

Provenance & Evidence