Sodium Bicarbonate → HCID 11775359, compound

Participants

Reaction Steps

A solution of 2-(3-amino-6-iodo-7-methyl-7H-pyrrolo[3,2-f]quinazolin-1-ylamino)-ethanol trifluoroactic acid salt (90 mg, 0.23 mmol) in ethylene glycol dimethyl ether (8.0 mL) and ethanol (4.0 mL) at 25° C. was treated with thiophene-2-boronic acid (60 mg, 0.47 mmol), a 2.0 M aqueous sodium bicarbonate solution (2.0 mL), and tetrakis(triphenylphosphine)-palladium (0) (5.0 mg). The resulting mixture was heated to reflux for 18 h. The resulting mixture was concentrated in vacuo and the residue suspended in acetonitrile and water and filtered. HPLC purification (21.2 mm×100 mm Zorbax CombiHT column using a 5:95 to 95:5 acetonitrile:water: 0.75% TFA gradient over 15 minutes) afforded 2-(3-amino-7-methyl-6-thiophen-2-yl-7H-pyrrolo[3,2-f]quinazolin-1-ylamino)-ethanol trifluoro-acetic acid salt as a light yellow solid; LRMS for C17H17N5O (M+H)+ at m/z=340.

Provenance & Evidence