Diisopropylethylamine → 2-amino-5-bromo-4-fluoro-N-methylbenzamide

A solution of 2-amino-5-bromo-4-fluorobenzoic acid (2.00 g, 8.55 mmol), methylamine hydrochloride (0.692 g, 10.2 mmol), TBTU (2.74 g, 8.55 mmol), and DIPEA (4.46 mL, 25.6 mmol) in DCM (15.0 mL) was stirred at rt for 30 minutes. The reaction was quenched with sat. aq. NaHCO3 (10 mL) and extracted with DCM (15 mL). The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to a yellow oil. The crude material was purified on a Teledyne ISCO Combiflash® Rf system using DCM/MeOH (100:0→95:5) as eluent to afford the title compound as 2.54 g of a white solid. 1H NMR (CDCl3, 400 MHz): δ 7.48 (d, J=7.3 Hz, 1H), 6.44 (d, J=10.4 Hz, 1H), 6.11 (br. s., 1H), 5.66 (br. s., 2H), 2.96 (d, J=4.8 Hz, 3H). MS (ESI): m/z 248.91 [M+H]+. UPLC: tR=3.26 min (ZQ3: polar—5 min).

1. customThe reaction was quenched with sat. aq. NaHCO3 (10 mL)
2. extractionextracted with DCM (15 mL)
3. washThe organic layer was washed with brine (10 mL)
4. dry with materialdried over anhydrous Na2SO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure to a yellow oil
7. customThe crude material was purified on a Teledyne ISCO Combiflash® Rf system

ORD record

ord-a841954fd94f4183b3e2da80597d9995

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133224B2