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

HRID 2252015Notes

Reaction equation

HRID 2252015 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([C:10]1[C:15](OS(C(F)(F)F)(=O)=O)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9].[F:28][C:29]([F:66])([F:65])[C:30]1[CH:31]=[C:32]([CH:58]=[C:59]([C:61]([F:64])([F:63])[F:62])[CH:60]=1)[CH2:33][N:34]1[C:38]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[C:37]([Sn](CCCC)(CCCC)CCCC)[N:36]=[N:35]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:64][C:61]([F:62])([F:63])[C:59]1[CH:58]=[C:32]([CH:31]=[C:30]([C:29]([F:28])([F:65])[F:66])[CH:60]=1)[CH2:33][N:34]1[C:38]([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[C:37]([C:15]2[C:10]([C:8]([C:7]3[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=3[Cl:5])=[O:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[N:36]=[N:35]1

Participants

7

Reactant 3

HCID 6212ChloroformHCID 85882776Trifluoro-methanesulfonic acid 2-(2-chloro-benzoyl)-pyridin-3-yl esterHCID 866012444-[3-(3,5-bis(trifluoromethyl)benzyl)-5-tributylstannanyl-3H-[1,2,3]triazol-4-yl]-pyridine

Product 1

HCID 10289930{3-[1-(3,5-bis-trifluoromethyl-benzyl)-5-pyridin-4-yl-1H-[1,2,3]triazol-4-yl]-pyridin-2-yl}-(2-chloro-phenyl)-methanoneYield 11%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

Add Pd2(dba)3.CHCl3 (42 mg, 0.04 mmol) to a degassed solution of trifluoro-methanesulfonic acid 2-(2-chloro-benzoyl)-pyridin-3-yl ester (149 mg, 0.41 mmol) and 4-[3-(3,5-bis-trifluoromethyl-benzyl)-5-tributylstannanyl-3H-[1,2,3]triazol-4-yl]-pyridine (296 mg, 0.45 mmol) in toluene (2 mL). Seal the mixture under N2 and heat at 120° C. for 2 hours. Add Pd(PPh3)4 (94 mg, 0.08 mmol), seal and heat at 120° C. for another 48 hours. Concentrate, dissolve in ACN, wash with hexanes (×3), dry over MgSO4 and concentrate. Purify the residue by flash chromatography on silica gel eluting with 0-10% ACN/Et2O to afford the title compound (26 mg, 11%) as tan solid. MS(IS) 588 (M+1). TLC: Rf=0.33 (10% ACN/Et2O).

Workup

  1. customSeal the mixture under N2
  2. temperatureheat at 120° C. for another 48 hours
  3. concentrationConcentrate
  4. dissolutiondissolve in ACN
  5. washwash with hexanes (×3)
  6. dry with materialdry over MgSO4
  7. concentrationconcentrate
  8. customPurify the residue by flash chromatography on silica gel eluting with 0-10% ACN/Et2O

Sources & evidence

ORD record
ord-8e6565be9ed94175863b7814513ac7bf
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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