Ammonium formate → 7-(3-(trifluoromethyl)pyridin-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)-1,8-naphthyridin-4-amine

HRID 1724843Notes

Reaction equation

HRID 1724843 reaction equation
Cl[C:2]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][N:14]=2)[C:9]2[C:4](=[N:5][C:6]([C:23]3[C:28]([C:29]([F:32])([F:31])[F:30])=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:7][CH:8]=2)[N:3]=1.C([O-])=O.[NH4+]>[Pd].CO>[F:32][C:29]([F:30])([F:31])[C:28]1[C:23]([C:6]2[N:5]=[C:4]3[C:9]([C:10]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][N:14]=4)=[CH:11][CH:2]=[N:3]3)=[CH:8][CH:7]=2)=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 575611422-chloro-7-[3-(trifluoromethyl)pyridin-2-yl]-N-[5-(trifluoromethyl) pyridin-2-yl]-[1,8]naphthyridin-4-amine

Product 1

HCID 462038647-(3-(trifluoromethyl)pyridin-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)-1,8-naphthyridin-4-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Stir a mixture of 2-chloro-7-[3-(trifluoromethyl)pyridin-2-yl]-N-[5-(trifluoromethyl) pyridin-2-yl]-[1,8]naphthyridin-4-amine (40 mg), ammonium formate (31 mg), 10% palladium on carbon (10 mg) in methanol (2 mL) at 50° C. for 2 hours. Cool, filter through Celite and evaporate to dryness. Purify by preparative thin layer chromatography, eluting with dichloromethane/methanol/ammonium hydroxide mixture to give the title compound. MS 436 (M+1). 1H NMR δ (CDCl3) 8.99 (1H, s), 8.84 (1H, d), 8.63 (1H, d), 8.61 (1H, s), 8.32 (1H, brs), 8.14 (1H, d), 8.05 (1H, brs), 7.79-7.85 (2H, m), 7.51 (1H, dd), 7.22 (1H,d).

Workup

  1. temperatureCool
  2. filtrationfilter through Celite
  3. customevaporate to dryness
  4. customPurify by preparative thin layer chromatography
  5. washeluting with dichloromethane/methanol/ammonium hydroxide mixture

Sources & evidence

ORD record
ord-a8770c906ab34bab91741017e49c6fb0
Source dataset
uspto-grants-2009_02
Patent number
US07488740B2

Reaction notes

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