3-Iodobenzoic acid → 3-iodo-N-(4-(trifluoromethoxy)phenyl)benzamide

DIPEA (6.34 mL, 36.3 mmol) was added to a solution of 3-iodobenzoic acid (3 g, 12.1 mmol) and 2-(6-chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU, 5.50 g, 13.31 mmol) in THF (25 mL) and MeCN (5 mL) and the RM was stirred at RT for 1 h. 4-(Trifluoromethoxy)aniline (2.435 mL, 18.14 mmol) was then added and the RM was stirred at RT for 3 h. The solvent was evaporated off under reduced pressure and the residue was treated with aq. HCl (50 mL of 1 M) and extracted with TBME/EtOAc (9:1). The combined extracts were washed with aq. 1 M HCl, sat. aq. Na2CO3 (50 mL), water and brine, dried over MgSO4 and the solvent was evaporated off under reduced pressure. The residue was suspended in water, filtered and dried to afford the title compound as a purple solid. UPLC-MS (Condition 1) tR=3.23 min, m/z=407.8-409.8 [M+H]+, m/z=405.9-406.9 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.33-7.41 (m, 3H) 7.88 (d, J=9.3 Hz, 2H) 7.94-8.00 (m, 2H) 8.30 (t, J=1.7 Hz, 1H) 10.50 (s, 1H).

1. stirringthe RM was stirred at RT for 3 h
2. customThe solvent was evaporated off under reduced pressure
3. additionthe residue was treated with aq. HCl (50 mL of 1 M)
4. extractionextracted with TBME/EtOAc (9:1)
5. washThe combined extracts were washed with aq. 1 M HCl, sat. aq. Na2CO3 (50 mL), water and brine
6. dry with materialdried over MgSO4
7. customthe solvent was evaporated off under reduced pressure
8. filtrationfiltered
9. customdried

ORD record

ord-79a33faf62bf4164ae39e1db6a400976

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315489B2