Potassium Phosphate, Tribasic → HCID 86706299, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (11.32 mg, 0.012 mmol) was added to a mixture of tert-butyl 2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (17) (37 mg, 0.088 mmol), potassium phosphate (62.1 mg, 0.29 mmol), 4-amino-N,N-dimethylbenzamide (16.68 mg, 0.10 mmol) and di-tBuX-Phos (15.75 mg, 0.037 mmol) in tert-BuOH containing 3% water (1.0 mL). The reaction mixture was heated at 80° C. for 1 h under microwave irradiation. More palladium catalyst (10.0 mg) and di-tBuX-Phos (8.0 mg) were added and the reaction mixture was heated at 80° C. for an additional 70 min under microwave irradiation. A final portion of palladium catalyst (4.0 mg) was added and the reaction mixture was heated at 80° C. for 70 min under microwave irradiation; it was then diluted with ethyl acetate (40 mL), washed with water (2×10 mL), dried (Na2SO4), and concentrated in vacuo. The residue was absorbed on silica gel (0.7 g), the free-running powder was placed on a 10 g isolute silica column. Elution with 60%, 70%, 80%, 90% ethyl acetate in hexane afforded the title compound (0.017 g) that was contaminated with the aniline starting material (4-amino-N,N-dimethylbenzamide) in a ratio of 1:1. 1H-NMR (500 MHz, CDCl3) 1.53 (s, 9H), 1.69 (s, 9H), 3.10 (s, 6H), 6.60 (d, J=0.6 Hz), 6.73 (br s, 1H), 7.39 (d, J=8.6 Hz, 2H), 7.45 (d, J=8.6 Hz, 2H), 7.70 (s, 1H), 7.83 (d, J=0.7 Hz, 1H), 8.23 (d, J=0.6 Hz, 1H), 8.50 (d, J=0.8 Hz, 1H). Also present were the following peaks consistent with the structure of the starting material, 4-amino-N,N-dimethylbenzamide: 3.06 (s, 6H), 3.84 (br s, 2H), 6.66 (d, J=8.6 Hz, 2H), 7.30 (d, J=8.6 Hz, 2H).

Provenance & Evidence