Ammonium Chloride → (5-Fluoro-2-nitrophenyl)-(5-fluoropyridin-3-yl)amine

HRID 243103

Reaction equation

CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=1.F[C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].[NH4+].[Cl-]>C1COCC1>[F:22][C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=2)[CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Alternative procedure: Potassium tert-butoxide (28.1 g, 0.25 mol) was added, in 2 portions, to a stirred solution of 3-amino-5-fluoropyridine (14.0 g, 0.125 mol) in anhydrous THF (400 mL) under a nitrogen atmosphere at 0° C. After 45 min stirring at 0° C., the resulting dark purple solution was transferred by cannula to a stirred solution of 2,4-difluoro-1-nitrobenzene (13.8 mL, 0.125 mol) in anhydrous THF (100 mL), at 0° C., over a period of 20 min. The resulting mixture was stirred for a further 45 min then poured onto a RT solution of NH4Cl (1:1 saturated solution:H2O, 1 L). The resulting yellow precipitate was filtered, washed with water and dried under vacuum at 50° C. to afford the title compound as an orange solid (18.2 g). The filtrate was partially evaporated, to remove some of the reaction solvent, the resulting precipitate was filtered then triturated with EtOAc to give a further 3.5 g of the title compound (overall 21.7 g, 69%) LCMS (Method C): RT 3.18 min [M+H]+ 252.13

Workup

stirringThe resulting mixture was stirred for a further 45 min
filtrationThe resulting yellow precipitate was filtered
washwashed with water
customdried under vacuum at 50° C.

Sources & evidence

ORD record: ord-48475f8f719d4c65873c9c3e29bf3c28
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Linked notes

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