Potassium Carbonate → 5-ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 1057100Notes

Reaction equation

HRID 1057100 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#[C:17][Si](C)(C)C)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.C([O-])([O-])=O.[K+].[K+]>CO>[C:16]([C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[N:8]=[CH:9]2)#[CH:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 667932011-(Tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-indazole

Product 1

HCID 866633655-ethynyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleYield 49.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 250-mL round-bottom flask equipped with a magnetic stir bar, a rubber septum, and a N2 inlet was charged with a solution of 1-(tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-indazole (12.6 g, 42.2 mmol) in MeOH. To this solution, solid K2CO3 (0.58 g, 4.2 mmol) was added in one portion. The resulting mixture was stirred at room temperature for 4 h. Upon completion by TLC, the reaction mixture was filtered, concentrated, and purified by silica gel chromatography (0-10% ethyl acetate in hexanes) to give the title compound (4.7 g) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 8.13 (s, 1H), 7.96 (s, 1H), 7.75 (d, 1H), 7.47 (dd, 1H), 5.86 (dd, 1H), 4.10 (s, 1H), 3.90-3.86 (m, 1H), 3.78-3.68 (m, 1H), 2.43-2.32 (m, 1H), 2.06-1.93 (m, 2H), 1.81-1.66 (m, 1H), 1.60-1.50 (m, 2H).

Workup

  1. customA 250-mL round-bottom flask equipped with a magnetic stir bar
  2. filtrationUpon completion by TLC, the reaction mixture was filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (0-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-984eb5c04b254dcb9f652a7901947d7f
Source dataset
uspto-grants-2016_07
Patent number
US09399646B2

Reaction notes

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