1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → Tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate

Participants

Reaction Conditions

Reaction Steps

Sodium tert-butoxide (21 mg, 0.213 mmol) was added to a mixture of 2-(4-iodophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (40.4 mg, 0.089 mmol), tert-butyl 3-aminopropanoate hydrochloride (19 mg, 0.107 mmol), Pd2(dba)3 (2.0 mg, 2.2 μmol), and Xantphos (5.1 mg, 8.9 μmol) in toluene (1.0 mL), and the resulting mixutre was heated under argon at 80° C. for 15 h. The reaction mixture was then cooled to 25° C. and concentrated onto silica gel. Chromatographic purificaiton (silica gel, 0-50% EtOAc/hexanes) furnished tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate as a yellow oil. MS (ESI) m/z: Calculated: 471.2; Observed: 472.1 (M++1).

Provenance & Evidence