Toluene → 7-(3,4-dichlorophenyl)-3-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]-7-methyl-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine

HRID 71156Notes

Reaction equation

HRID 71156 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9](O)([CH2:11][CH2:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[N:25][C:24]([CH3:27])=[N:23]3)=[C:18]([O:28][CH3:29])[CH:17]=2)[CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].C[Si]([N:35]=[N+:36]=[N-:37])(C)C.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([CH3:10])[N:35]3[N:36]=[N:37][C:15]([C:16]4[CH:21]=[CH:20][C:19]([N:22]5[CH:26]=[N:25][C:24]([CH3:27])=[N:23]5)=[C:18]([O:28][CH3:29])[CH:17]=4)=[C:14]3[CH2:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78378AzidotrimethylsilaneHCID 66608944HCID 66608944, compound

Product 1

HCID 666042607-(3,4-dichlorophenyl)-3-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]-7-methyl-4,5,6,7-tetrahydro[1,2,3]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Boron trifluoride-diethyl ether complex (75.3 μL) was added to a mixture of 2-(3,4-dichlorophenyl)-7-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hept-6-yn-2-ol (88.0 mg), trimethylsilylazide (105 μL) and toluene (4 mL) under ice-cooling, and the mixture was stirred at room temperature for 30 min, at 70° C. for 15 min and at 110° C. for 6 hr, and allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate, the mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (15.7 mg).

Workup

  1. temperaturecooling
  2. temperatureto cool to room temperature
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-40d6a79b15a4486a83fc06aed09d6fc3
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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