Dimethylformamide → N-{6-[5-[(2-Hydroxypropanoyl)amino]-6-(methyloxy)-3-pyridinyl]-1H-indazol-4-yl}-2-methyl-1,3-thiazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-Methyl-N-[1-(phenylsulfonyl)-6-(trimethylstannanyl)-1H-indazol-4-yl]-1,3-thiazole-4-carboxamide (150 mg, 0.267 mmol), N-[5-bromo-2-(methyloxy)-3-pyridinyl]-2-hydroxypropanamide (88 mg, 0.321 mmol) and Pd(PPh3)4 (31 mg, 0.027 mmol) were weighed to a microwave vial. DMF (3 ml) was added and the reaction was heated in the microwave at 120° C. for 30 mins, then again at 120° C. for a further for 30 mins. The reaction mixture was passed through a 1 g silica cartridge, pre-conditioned with methanol, washing with methanol. The solvent was evaporated in the blow down. The residue was dissolved in DMSO:methanol (1 ml, 1:1, v/v) and purified by MDAP (Method E). Pure fraction was evaporated to dryness. The residue was dissolved in IPA and 2M NaOH (aq) and left overnight. The reaction was concentrated in vacuo, then neutralised using 2M HCl (aq) and the resultant precipitate was collected by filtration. The material was dissolved in DMSO:methanol (0.7 ml, 1:1, v/v) and purified by MDAP (Method E). Pure fractions were combined and evaporated to dryness to afford the title compound (10 mg).

Provenance & Evidence