p-Toluidine → HCID 68290942, compound

Participants

Reaction Steps

tert-Butyl-2-(1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl)-6-chloro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (17) (44 mg 0.105 mmole) and 4-methylaniline (13 mg 0.12 mmole) were placed in a microwave vial and potassium phosphate (53 mg 0.25 mmole), XantPhos (10.5 mg 0.022 mmol) and Pd2(dba)3 (10.1 mg 0.011 mmol) were added. NMP containing water (3%) (1.2 mL) was then added and the vial sealed under argon. It was microwaved at 80° C. for 1.5 hrs. The reaction was added to water (10 mL) and extracted with ethyl acetate (3×6 mL). The combined organics were washed with water (3×5 mL) and with brine, dried and evaporated. The residue was applied to three 1 mm 20×20 cm silica prep tlc plates, which were twice eluted with 1:2 ethyl acetate:cyclohexane. The product band was recovered using acetone to give the product (17 mg). 1H-NMR (CDCl3, 500 MHz): δ 1.51 (s, 9H), 1.70 (s, 9H), 2.36 (s, 3H), 6.58 (m, 1H), 6.68 (br s, 1H, NH), 7.18 (d, J=8.20 Hz, 1H), 7.25 (d, J=8.51 Hz, 2H), 7.54 (m, 1H), 7.83 (d, J=0.63 Hz, 1H), 8.23 (s, 1H), 8.44 (m, 1H). ESI-HRMS Found 490.2452, calculated for C27H32N5O4 [M+H]+: 490.2449.

Provenance & Evidence