1,2-Dichloroethane → HCID 57755916, compound

Participants

Reaction Conditions

Reaction Steps

The product of step (a) (4.03 g, 13.69 mmol, 1 equiv) and NaOH (2.5 N, 20 mL) were dissolved in methanol (60 mL) and heated to 60° C. in a sealed tube for four hours. The reaction mixture was diluted with water (˜50 mL) and EtOAc (˜50 mL), stirred, and separated. The aqueous layer was brought to pH 1 with 2N HCl and extracted with EtOAc. The organic layer was concentrated en vacuo and the residue (650 mg, 2.32 mmol, 1 equiv) was dissolved in DMF (13 mL). 5-aminoindazole (376 mg, 2.78 mmol, 1.2 equiv), EDC (531 mg, 2.78 mmol, 1.2 equiv), Et3N (780 μL, 5.57 mmol, 2.4 equiv) and catalytic DMAP (5 mg) were added and the mixture was heated to 80° C. in a sealed tube for two hours. The residue was dissolved in EtOAc and water and extracted. The organic layer was washed with 1N HCl, satd. NaHCO3 and Brine. The organic layer was concentrated en vacuo and then triturated with CH2Cl2/Hexane to give 368 mg of the title compound as a beige powder (40%). MS (ES+) m/e 396 [M+H]+

Provenance & Evidence