N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide → N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-amino-dibenzo[b,d]furan-1-carboxamide

Participants

Reaction Steps

Second, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with Raney Nickel. In particular, to a 500 mL pressure vessel was added N′-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (2.00 g, 4.27 mmol), DMF (30.0 mL) and Raney Nickel (1.79 g). The reaction mixture was hydrogenated (50 psi) for 23 h (reaction monitored by HPLC). The reaction mixture was filtered, washed with DMF (20 mL) and the filtrate concentrated to a 5 mL volume (distilled below 70° C. under vacuum). Water (33.0 mL) was added, the precipitate filtered, washed with water (20 mL) and dried in a vacuum oven (65° C.) to yield the amine as a cream colored solid (1.67 g, 91.3%). Purity 98.67% by HPLC.

Provenance & Evidence