Lawesson's reagent → N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine

HRID 1518527Notes

Reaction equation

HRID 1518527 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][C:11]=1[NH:16][C:17]([C:19]1[C:20]([NH:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=1)=O.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)S2)=CC=1>O1CCOCC1>[C:26]([NH:25][C:20]1[C:19]([C:17]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[C:10]3[CH:15]=[CH:14][N:13]=[CH:12][C:11]=3[N:16]=2)=[CH:24][CH:23]=[CH:22][N:21]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 58179766N-(4-(2,3-difluorophenylamino)pyridin-3-yl)-2-(tert-butylamino)pyridine-3-carboxamide

Product 1

HCID 58179805N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amineYield 41.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of N-(4-(2,3-difluorophenylamino)pyridin-3-yl)-2-(tert-butylamino)pyridine-3-carboxamide (3.0 g, 7.55 mmol) in 1,4-dioxane (50 mL) was added 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's reagent, 4.5 g, 11.3 mmol) at room temperature. The reaction mixture was heated at reflux (110° C.) for 10 hr. The reaction mixture was concentrated in vacuo and the resulting residue was taken in saturated aq. NaHCO3 solution (100 mL) and extracted with CHCl3 (200 mL). The organics were washed with water (3×100 mL), brine solution (1×100 mL), and dried (Na2SO4). Filtration and evaporation of solvent in vacuo, followed by silica gel chromatography (0.5% methanol/chloroform) gave N-tert-butyl-3-(1-(2,3-difluorophenyl)-1H-imidazo[4,5-c]pyridin-2-yl)pyridin-2-amine (1.2 g, 41.9% yield) as a light yellow solid; LC-MS: 380.2 (M+H).

Workup

  1. temperatureThe reaction mixture was heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with CHCl3 (200 mL)
  4. washThe organics were washed with water (3×100 mL), brine solution (1×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and evaporation of solvent in vacuo

Sources & evidence

ORD record
ord-286626e4e95c4738a95e68ad880f5c02
Source dataset
uspto-grants-2012_07
Patent number
US08232406B2

Reaction notes

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