Water → 6-amino-5-ethynyl-1H-indazole-7-carboxylic acid methyl ester

HRID 245624Notes

Reaction equation

HRID 245624 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:20])=[C:7]([C:14]#[C:15][Si](C)(C)C)[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OC)(C)(C)C>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([NH2:20])=[C:7]([C:14]#[CH:15])[CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[CH:10]2)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 2724141Tetrabutylammonium FluorideHCID 579901606-amino-5-trimethylsilanylethynyl-1H-indazole-7-carboxylic acid methyl ester

Product 1

HCID 579901016-amino-5-ethynyl-1H-indazole-7-carboxylic acid methyl esterYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 500 mg (1.74 mmol) of 6-amino-5-trimethylsilanylethynyl-1H-indazole-7-carboxylic acid methyl ester in 17 mL of anhydrous tetrahydrofuran under an atmosphere of argon is added 2.6 mL (2.6 mmol) of a 1 M solution tetrabutylamonium fluoride in tetrahydrofuran. The reaction mixture is stirred at ambient temperature for 2 hours. Water and tert-butylmethylether are added and the two phases are separated. The aqueous layer is extracted with tert-butylmethylether. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is suspended in hexanes. Filtration affords 210 mg (56%) of the product as a yellowish solid; LC/MS:216/217 (M+H)+.

Workup

  1. customthe two phases are separated
  2. extractionThe aqueous layer is extracted with tert-butylmethylether
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. filtrationFiltration

Sources & evidence

ORD record
ord-af1b74951a614ca2a6e65d47832f736f
Source dataset
uspto-grants-2014_02
Patent number
US08658801B2

Reaction notes

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