Methylamine → HCID 24696192, compound

To a mixture of 5-bromo-2-fluorobenzoic acid (200 mg, 0.91 mmol) in dichloromethane (5 mL) was added oxalyl chloride (0.16 mL, 1.8 mmol), followed by 1 drop of N,N-dimethylformamide. The reaction was stirred at room temperature for 1.5 hours. The reaction was concentrated and the resulting residue was dissolved in dichloromethane (3 mL) and cooled to 0° C. Methylamine (2.3 mL, 5 mmol, 2 M in tetrahydrofuran) was added and the reaction was allowed to stir at 0° C. for 30 minutes. The reaction was quenched with water and the mixture was concentrated. The residue was diluted with water and the resulting solids were filtered, rinsed with water, and dried under vacuum to give the title compound (196.6 mg, 93%) as a white solid. +ESI (M+H+1) 234.1; 1H NMR (400 MHz, CDCl3, δ); 8.22 (dd, J=6.83, 2.73 Hz, 1H), 7.55 (ddd, J=8.68, 4.49, 2.63 Hz, 1H), 7.00 (dd, J=11.32, 8.58 Hz, 1H), 6.67 (br. s., 1H), 3.02 (dd, J=4.88, 1.17 Hz, 3H).

1. concentrationThe reaction was concentrated
2. dissolutionthe resulting residue was dissolved in dichloromethane (3 mL)
3. temperaturecooled to 0° C
4. stirringto stir at 0° C. for 30 minutes
5. customThe reaction was quenched with water
6. concentrationthe mixture was concentrated
7. additionThe residue was diluted with water
8. filtrationthe resulting solids were filtered
9. washrinsed with water
10. customdried under vacuum

ORD record

ord-5a543f5a6b4e46f5af4c6a6402e547c2

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181252B2