Sodium Carbonate → N-[3-(3-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl]prop-2-enamide

Temperature

90 °C

A solution of 19 (50 mg, 0.2369 mmol) and 2 (50 mg, 0.2369 mmol) in ethanol and toluene (1:4 mL) was added sodium carbonate (49.74 mg, 0.4738 mmol). The reaction was degassed and purged with nitrogen for 15 min. Pd(dppf)Cl2.DCM (9.06 mg, 0.0114 mmol), and again degassed for 15 min. The reaction mixture was stirred for 2 h at 90° C. and the reaction mixture allowed to cool to rt and diluted with DCM (25 mL). The organic layer was filtered through Celite and concentrated to get the crude. The resulting oil was purified via silica gel chromatography using a gradient of 30% ethyl acetate:hexane to afford Compound 20. MS-ES+277 1H NMR (400 MHz, DMSO-D6) 20: 11.37 (d, 1H), 10.24 (d, 1H), 8.45 (d, 1H), 8.09 (d, 2H), 7.68 (d, 1H), 7.43 (d, 2H), 7.28 (d, 1H), 6.46 (d, 1H), 6.44 (d, 1H), 5.79 (d, 1H), 2.30 (d, 1H).

1. customThe reaction was degassed
2. custompurged with nitrogen for 15 min
3. temperatureto cool to rt
4. filtrationThe organic layer was filtered through Celite
5. concentrationconcentrated
6. customto get the crude
7. customThe resulting oil was purified via silica gel chromatography

ORD record

ord-f3d918c6ae28492aba217855d6b9c3a3

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206188B2