Triethylamine → HCID 57721368, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-methylnicotinic acid (500 mg, 2.9 mmol) was suspended in CH2Cl2 (14.6 mL). Oxalyl chloride (0.3 mL, 3.5 mmol) was added followed by 3 drops of DMF and the reaction was stirred at 23° C. for 2 h. The solvent was removed by rotary evaporation and the residue was dried under vacuum. The crude acid chloride was dissolved in CH3CN (14 mL) and 2,4-difluorobenzenamine (0.33 mL, 3.2 mmol) was added followed by triethylamine (0.41 mL, 2.9 mmol). The reaction was stirred at 23° C. for 16 h and then concentrated in vacuo. The residue was partitioned between EtOAc (30 mL) and sat. aq. NaHCO3 soln (30 mL). A little water was added to help break up some of the residual salts. The aqueous layer was extracted with EtOAc (3×30 mL). The combined organics were dried over MgSO4 and concentrated in vacuo. Trituration with hot 5% EtOAc-hexanes afforded the desired product as a light tan powder (559 mg, 68%). 1H NMR (400 MHz, CDCl3) δ 2.60 (s, 3H), 6.82-7.09 (m, 2H), 7.22-7.32 (d, 1H, J=7.63 Hz), 8.18 (d, 1H, J=8.14 Hz), 8.28-8.50 (m, 1H), 8.57 (s, 1H).

Provenance & Evidence