2-Fluoroaniline → HCID 178461246, compound

HRID 81186Notes

Reaction equation

HRID 81186 reaction equation
Br[C:2]1[N:19]([CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]2)[C:5]2[C:6]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)=[N:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=1.[F:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[Cl:18][C:16]1[CH:17]=[C:12]([C:6]2[C:5]3[N:19]([CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([CH3:27])[CH2:23][CH2:22]4)[C:2]([NH:31][C:30]4[CH:32]=[CH:33][CH:34]=[CH:35][C:29]=4[F:28])=[N:3][C:4]=3[CH:9]=[C:8]([C:10]#[N:11])[N:7]=2)[CH:13]=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 95842-FluoroanilineHCID 10796Cesium carbonateHCID 178461197HCID 178461197, compound

Product 1

HCID 178461246HCID 178461246, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a sealed tube were added 2-bromo-4-(5-chloropyridin-3-yl)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile (Preparative Example 3.1) (0.010 g, 0.045 mmol), 2-fluoroaniline (0.0050 g, 0.045 mmol), Cs2CO3 (0.022 g, 0.067 mmol), chloro[(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2′-amino-1,1′-biphenyl)]palladium(11) (0.0050 g, 0.0056 mmol), and dioxane (0.5 mL). The reaction vessel was purged with argon, sealed and warmed to 75° C. for 8 hours with stirring. The reaction was cooled and diluted with dioxane (1.0 mL) and was passed through a syringe filter. The collected eluent was concentrated in vacuo to afford 4-(5-chloropyridin-3-yl)-2-((2-fluorophenyl)amino)-3-((trans-4-methylcyclohexyl)methyl)-3H-imidazo[4,5-c]pyridine-6-carbonitrile as a crude residue. MS ESI calc'd. for C26H24ClFN6 [M+H]+ 475. found 475.

Workup

  1. customThe reaction vessel was purged with argon
  2. customsealed
  3. temperatureThe reaction was cooled
  4. additiondiluted with dioxane (1.0 mL)
  5. customwas passed through a syringe
  6. filtrationfilter
  7. concentrationThe collected eluent was concentrated in vacuo

Sources & evidence

ORD record
ord-a671aaebeebe471fb8e9cfb1a0479c95
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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