Isopropylamine → HCID 82547469, compound

To a slurry of 2-amino-3-bromobenzoic acid (Aldrich; 1.00 g, 4.63 mmol) in 10 mL EtOAc in an ice bath was added 1-propanephosphonic acid cyclic anhydride (50 wt % in EtOAc; Matrix Scientific; 3.00 mL, 5.09 mmol) followed by isopropylamine (1.19 mL, 13.89 mmol). The ice bath was removed and the solution stirred rapidly at RT. A precipitate formed. After 30 min, the reaction was judged complete. The reaction was partitioned between sat'd aq. NaHCO3 and EtOAc. The organic layer was washed with sat'd aq. NaHCO3 once, sat'd NaCl once, and the organics were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give 2-amino-3-bromo-N-isopropylbenzamide (1.00 g, 3.89 mmol, 84% yield) as a white solid: 1H NMR (400 MHz, CDCl3) δ ppm 7.51 (2H, dd, J=7.9, 1.5 Hz), 7.25 (1H, d, J=1.4 Hz), 6.53 (2H, t, J=7.8 Hz), 5.72-6.15 (3H, m), 4.15-4.33 (1H, m), 1.27 (7H, d, J=6.7 Hz). m/z (ESI, +ve) 257.0/259.0 (M+H)+.

1. customThe ice bath was removed
2. customA precipitate formed
3. customThe reaction was partitioned between sat'd aq. NaHCO3 and EtOAc
4. washThe organic layer was washed with sat'd aq. NaHCO3 once
5. dry with materialthe organics were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-b152ebdebd3842ebb01e47e4a1bdf04e

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394297B2