Potassium Carbonate → HCID 66898783, compound

HRID 19383Notes

Reaction equation

HRID 19383 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[N:3]1.[CH2:12]([O:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:12]([O:14][C:15](=[O:19])/[CH:16]=[C:17](/[O:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[N:3][N:2]2[CH3:1])\[CH3:18])[CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 78043Ethyl 2-butynoateHCID 1354635691-Methyl-1H-indazol-4-ol

Product 1

HCID 66898783HCID 66898783, compoundYield 74.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-methyl-1H-indazol-4-ol (0.130 g, 0.88 mmol), ethyl-2-butynoate (0.59 g, 5.26 mmol), a catalytic amount of 4-dimethylaminopyridine, and potassium carbonate (0.120 g, 0.88 mmol) in tetrahydrofuran (10 mL) in a sealed tube was heated at 80° C. for 14 h. The reaction mixture was then filtered. The solids were washed with a small amount of tetrahydrofuran and the combined filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel 0% to 40% ethyl acetate/hexanes) which afforded (E)-3-(1-methyl-1H-indazol-4-yloxy)-but-2-enoic acid ethyl ester (0.170 g, 74%) as a viscous tan oil.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. washThe solids were washed with a small amount of tetrahydrofuran
  3. concentrationthe combined filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography (silica gel 0% to 40% ethyl acetate/hexanes) which

Sources & evidence

ORD record
ord-4f876e381c454d318e43986881159972
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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