Nitrogen → 5-Ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazole

HRID 1057104Notes

Reaction equation

HRID 1057104 reaction equation
N#N.[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[N:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]#[C:19][Si](C)(C)C)=[CH:17][C:12]=2[N:11]=[N:10]1.C([O-])([O-])=O.[K+].[K+]>CO>[C:18]([C:16]1[CH:15]=[CH:14][C:13]2[N:9]([CH:4]3[CH2:5][CH2:6][CH2:7][CH2:8][O:3]3)[N:10]=[N:11][C:12]=2[CH:17]=1)#[CH:19]

Participants

5

Reactant 3

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 668021201-(Tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-benzo[d][1,2,3]triazole

Product 1

HCID 866952825-Ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d][1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100-mL round-bottom flask equipped with a magnetic stir bar, a rubber septum and N2 inlet was charged with a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-benzo[d][1,2,3]triazole (3.5 g, 11.7 mmol) in MeOH (59 mL). To this solution, solid K2CO3 (0.16 g, 1.17 mmol) was added in one portion. The resulting mixture was stirred at room temperature for 5 h. Reaction was monitored by TLC. Upon completion, the reaction mixture was filtered and concentrated to give the crude material. This crude product was purified on a silica gel column eluted with 5% ethyl acetate in hexanes affording the title compound as a pale yellow solid (2.6 g). LCMS: 144 [(M-THP+H)+H]+.

Workup

  1. customA 100-mL round-bottom flask equipped with a magnetic stir bar
  2. customReaction
  3. filtrationUpon completion, the reaction mixture was filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b28186a09f1d43aba3aa513db72bf443
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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