Methanol → HCID 178435597, compound

HRID 598870Notes

Reaction equation

HRID 598870 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[C:12][Si](C)(C)C)[CH:9]=2)[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CO>C1COCC1>[C:11]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][N:3]=[C:2]2[CH3:1])#[CH:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 178434278HCID 178434278, compound

Product 1

HCID 178435597HCID 178435597, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-5-(2-(trimethylsilyl)ethynyl)-1H-indazole (820 mg, 3.55 mmol) was dissolved in 20 mL THF and K2CO3 (4.9 g, 35.5 mmol) and 200 mL MeOH were added. The mixture was stirred for 1 hour at room temperature, filtered and evaporated. The mixture was purified via glass column chromatography (35% EtOAc in hexane) and the title compound (500 mg, 3.2 mmol) was obtained as a light yellow solid. LCMS (API-ES) m/z (%): 157.0 (100%, M++H).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe mixture was purified via glass column chromatography (35% EtOAc in hexane)

Sources & evidence

ORD record
ord-949d704a4c884e1699a6f3c80a2715a8
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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