(2-Bromopyridin-3-yl)-(2-chlorophenyl)methanone → {2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-methyl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanone

HRID 2251992

Reaction equation

HRID 2251992 reaction equation
Br[C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:17][C:18]([F:50])([F:49])[C:19]1[CH:20]=[C:21]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:22][N:23]1[C:27]([CH3:28])=[C:26]([Sn](CCCC)(CCCC)CCCC)[N:25]=[N:24]1>CN(C=O)C>[F:50][C:18]([F:17])([F:49])[C:19]1[CH:20]=[C:21]([CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[CH:44]=1)[CH2:22][N:23]1[C:27]([CH3:28])=[C:26]([C:2]2[C:7]([C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[N:25]=[N:24]1

Participants

4

Reactant 2

HCID 85882881(2-Bromopyridin-3-yl)-(2-chlorophenyl)methanoneHCID 866012501-(3,5-bis-trifluoromethyl-benzyl)-5-methyl-4-tributylstannanyl-1H-[1,2,3]triazole

Product 1

HCID 59644543{2-[1-(3,5-bis-trifluoromethyl-benzyl)-5-methyl-1H-[1,2,3]triazol-4-yl]-pyridin-3-yl}-(2-chloro-phenyl)-methanoneYield 54.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve (2-bromo-pyridin-3-yl)-(2-chloro-phenyl)-methanone (148 mg, 0.50 mmol) and 1-(3,5-bis-trifluoromethyl-benzyl)-5-methyl-4-tributylstannanyl-1H-[1,2,3]triazole (449 mg, 0.75 mmol) in DMF (5 mL) and degass, then add dichlorobis(triphenylphosphine) palladium (70 mg, 0.10 mmol). Seal the mixture under N2 and heat at 80° C. for 24 hours. Concentrate, dissolve in CHCl3, wash with saturated potassium fluoride solution (2×), saturated potassium bicarbonate solution, brine, dry over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexane followed by recrystallization from EtOAc/hexane to afford the title compound (142 mg, 54%). MS(IS) 525 (M+1); TLC (60% EtOAc/hexane) Rf=0.30.

Workup

  1. customdegass
  2. customSeal the mixture under N2
  3. concentrationConcentrate
  4. dissolutiondissolve in CHCl3
  5. washwash with saturated potassium fluoride solution (2×), saturated potassium bicarbonate solution, brine
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting with 0-40% EtOAc/hexane
  9. customfollowed by recrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-5336a7072567493f9c1fd83e095dbb6a
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Linked notes

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