3-Iodobenzoic acid → 3-Iodobenzamide

To a stirred solution of 3-iodobenzoic acid (2.00 g, 8.06 mmol) and DIPEA (562 mL, 32.3 mmol) in MeCN (100 mL) at room temperature was added HOBT (1.63 g, 12.1 mmol) and EDCI.HCl (2.32 g, 12.1 mmol). After stirring for 10 minutes, ammonium carbonate (4.65 g, 48.4 mmol) was added and the resulting solution was stirred overnight. The volatiles were removed in vacuo to yield a crude solid which was suspended in water (100 mL). The resulting suspension was sonicated for 10 minutes then the solid collected by filtration. The filter cake was washed with water (20 mL) and dried to yield the title compound (I29) (1.65 g 83%) as a brown solid; 1H NMR (400 MHz, CDCl3) δ 8.13 (t, J=1.6 Hz, 1H), 7.83 (ddd, J=7.9, 1.7, 1.1 Hz, 1H), 7.73 (ddd, J=7.8, 1.7, 1.1 Hz, 1H), 7.16 (t, J=7.8 Hz, 1H), 6.18-5.49 (m, J=137.3 Hz, 2H). LCMS Method C: rt=5.04 min; m/z=248 [M+1]+.

1. stirringthe resulting solution was stirred overnight
2. customThe volatiles were removed in vacuo
3. customto yield a crude solid which
4. customThe resulting suspension was sonicated for 10 minutes
5. filtrationthe solid collected by filtration
6. washThe filter cake was washed with water (20 mL)
7. customdried

ORD record

ord-b7304c64d08f4326b1609b06556039cf

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174946B2