Cesium carbonate → HCID 67470491, compound

Participants

Reaction Conditions

Reaction Steps

A mixture N-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-1H-pyrazolo[4,3-b]pyridin-7-amine and N-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-yl)-2H-pyrazolo[4,3-b]pyridin-7-amine (54 mg, 0.162 mmol) and Cs2CO3 (52.6 mg, 0.162 mmol) were stirred in DMF (2 mL) for 5 minutes. 2-Bromo-N-methylacetamide (24.55 mg, 0.162 mmol) was added; the vessel was sealed and heated in a microwave at 85° C. for 35 minutes. The reaction mixture was cooled and purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 20-30% acetonitrile (containing 10 mM NH4HCO3) in water (containing 10 mM NH4HCO3) to give 2-(7-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-ylamino)-1H-pyrazolo[4,3-b]pyridin-1-yl)-N-methylacetamide: 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.46 (s, 3H) 2.58 (s, 3H) 2.78 (s, 3H) 5.23 (s, 2H) 7.01 (d, J=4 Hz, 1H) 7.30-7.42 (m, 1H) 7.56-7.67 (m, 1H) 7.96 (s, 1H) 8.32 (d, J=4 Hz, 1H) 8.45 (s, 1H) 8.52 (s, 1H); MS [M+H] found 406.4; and 2-(7-(3′-fluoro-5,6′-dimethyl-2,2′-bipyridin-4-ylamino)-2H-pyrazolo[4,3-b]pyridin-2-yl)-N-methylacetamide; 1H NMR (400 MHz, METHANOL-d4) δ ppm 2.42 (s, 3H) 2.54 (s, 3H) 2.75 (s, 3H) 5.24 (s, 2H) 7.29-7.41 (m, 2H) 7.52-7.59 (m, 1H) 7.61 (d, J=4 Hz, 1H) 8.18 (s, 1H) 8.40 (s, 2H); MS [M+H] found 406.4.

Provenance & Evidence