Diisopropylethylamine → HCID 67508334, compound

Participants

Reaction Steps

To a solution of acid anhydride (0.89 mL, 9.4 mmol) in DMF (10 mL) in a pressure tube was added sodium formate (0.96 g, 14.2 mmol) and Hunig's base (1.6 mL, 9.4 mmol). The pressure tube was sealed and the mixture allowed to stir at room temperature for 45 minutes. The tube was opened and a solution of [1-(5-iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (1.7 g, 4.7 mmol) in DMF (3 mL) was added followed by LiCl (0.60 g, 14.2 mmol) and Pd(OAc)2 (0.11 g, 0.47 mmol). The reaction vessel was sealed and the mixture heated at 80° C. for 20 h. The reaction mixture was cooled to room temperature and the cap slowly removed allowing for gas release. The mixture was diluted with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, 1N HCl, brine and dried with MgSO4. The mixture was filtered and concentrated to give 6-(1-tert-butoxycarbonylamino-cyclopropyl)-nicotinic acid (0.51 g, 1.8 mmol) as a yellow solid, m/z 279.6.

Provenance & Evidence