Diisopropylethylamine → HCID 67508334, compound

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.

1. customThe pressure tube was sealed
2. customThe reaction vessel was sealed
3. temperaturethe mixture heated at 80° C. for 20 h
4. temperatureThe reaction mixture was cooled to room temperature
5. customthe cap slowly
6. customremoved
7. additionThe mixture was diluted with water
8. extractionextracted with EtOAc (3×100 mL)
9. washThe combined extracts were washed with water, 1N HCl, brine
10. dry with materialdried with MgSO4
11. filtrationThe mixture was filtered
12. concentrationconcentrated

ORD record

ord-9abfdea98e824359b1866aed9c29fb7e

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575360B2