Reaction #175

Reaction equation

O=C(Nc1cc(Cl)ccn1)C1

Nc1cccc2c1OCO2

→

O=C(Nc1cc(Nc2cccc3c2

Yield 50.7%

Solvents

CC(=O)N(C)C

Conditions

Procedure

benzo[d][1,3]dioxol-4-amine (100 mg, 0.73 mmol), N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (143 mg, 0.73 mmol), XANTPHOS (50.6 mg, 0.09 mmol), PALLADIUM(II) ACETATE (8.19 mg, 0.04 mmol) and CESIUM CARBONATE (475 mg, 1.46 mmol) were suspended in DMA (3mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 1.5 hours in the microwave reactor and cooled to RT. LC/MS showed completion. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 0.35M NH3/MeOH and pure fractions were evaporated to dryness to afford N-(4-(benzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)cyclopropanecarboxamide as a brown oil. The crude product was purified by preparative HPLC using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(4-(benzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)cyclopropanecarboxamide (110 mg, 50.7 %) as a cream solid.

Source