Sodium Bicarbonate → HCID 58255801, compound

Participants

Reaction Conditions

Reaction Steps

N-(6-Bromo-1H-indazol-4-yl)-2-methyl-1,3-thiazole-4-carboxamide (200 mg, 0.59 mmol), bis(pinacolato)diboron (166 mg, 0.652 mmol), Pd(dppf)Cl2 (48 mg, 0.06 mmol) and potassium acetate (175 mg, 1.78 mmol) were combined in a microwave vial and DMA (10 ml) was added. The solution was degassed and then heated in a Biotage initiator at 80° C. for 20 minutes. More Pd(dppf)Cl2 (48.4 mg, 0.059 mmol) was added, the solution was degassed and heated again at 80° C. for 20 minutes. 4-Bromo-2-pyridone (206 mg, 1.19 mmol), Pd(PPh3)4 (34 mg, 0.03 mmol) and sodium bicarbonate (0.89 ml, 1.78 mmol) were added to the mixture, which was heated under microwave conditions at 150° C. for 15 minutes. Saturated sodium bicarbonate (100 ml) was added to the mixture. The resulting suspension was washed three times with ethyl acetate (100 ml each). A spatula of sodium chloride was added to improve layer separation. Organics were dried and filtered with a hydrophobic frit, combined and dried under vacuum. The solid obtained was preabsorbed on silica and purified on silica (Si) 100 g using a 0-15% methanol-DCM over 60 mins. Appropriate fractions were combined and dried under vacuum. The sample was dissolved in DMSO (1 ml) and purified by MDAP (Method B) eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid). Pure fractions were combined and dried under vacuum to afford the title compound (10 mg).

Provenance & Evidence