3-Chloro-2-fluoroaniline → HCID 16046861, compound

Participants

Reaction Steps

Steps 6 and 7: A sample of 3,3-dimethyl-1-oxo-indan-5-carbonitrile and (4′-Fluoro-3′-methyl-biphenyl-3-yl)-hydrazine hydrochloride (prepared as in example 70, steps 1 and 2 except using 3-methyl-4-fluorophenylboronic acid and 3-chloro-2-fluoroaniline as the coupling partners) are reacted together as in example 1, step 3. The crude product is then subjected to hydrolysis as in example 19, step 3 to afford 6-fluoro-7-(4-fluoro-3-methyl-phenyl)-10,10-dimethyl-5,10-dihydro-indeno[1,2-b]indole-2-carboxylic acid amide as a light yellow solid: 1H NMR (400 MHz, acetone-d6) δ 11.18 (s, 1H), 8.14 (s, 1H), 7.95 (dd, 1H, J=1.2, 7.6 Hz), 7.68 (d, 1H, J=8 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.54 (dd, 1H, J=0.8, 7.6 Hz), 7.46-7.45 (m, 2H), 7.20-7.25 (m, 2H), 6.65-6.50 (br, 2H), 225 (d, 3H, J=1.6 Hz), 1.66 (s, 6H), ESMS 77/z 403.2 (M+H+).

Provenance & Evidence