4-Bromo-2-fluoroaniline → HCID 68546216, compound

Participants

Reaction Conditions

Reaction Steps

Combine diethyl-(4-imidazo[1,2-a]pyridin-7-yl-pyridin-2-ylmethyl)-amine (1.00 g, 3.57 mmol), 4-bromo-2-fluoro-phenylamine (1.36 g, 7.13 mmol) and potassium acetate (0.700 g, 7.13 mmol) in DMSO (4 mL). De-gas the mixture for 10 minutes with N2. Add dichlorobis(triphenylphosphine) palladium (II) (0.250 g, 0.357 mmol); stir the reaction mixture for 14 hours under N2 at 100° C. Purify using an SCX cartridge (10 g VARIAN bond elut), eluting with 1:1 methanol:dichloromethane, then 1:1 2 M NH3 in methanol:dichloromethane. Purify via reverse phase chromatography using a 25 cm by 50.8 mm (i.d.) column w/10 micron particles (MeCN/0.03% HCl H2O (5:95) to 100% MeCN; 30 min). Compound obtained is partitioned between ethyl acetate and 1 N NaOH. Wash the organic layer with aqueous saturated sodium chloride, dry over magnesium sulfate, filter, and concentrate to afford the title compound (0.286 g, 21%). MS(ES), m/z 390 (M+1).

Provenance & Evidence