Potassium Carbonate → HCID 178520817, compound

HRID 1768567Notes

Reaction equation

HRID 1768567 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][CH2:26][OH:27]>C(C(C)=O)C(C)C>[OH:27][CH2:26][CH2:25][CH2:24][N:14]1[CH2:15][CH2:16][CH:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([F:1])=[CH:3][CH:4]=3)[NH:8][N:7]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 178505426HCID 178505426, compound

Product 1

HCID 178520817HCID 178520817, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

To a mixture of 6-fluoro-3-(4-piperidinyl)-1H-indazole (438 mg, 2 mmol) and dry potassium carbonate (1.1 g, 6 mmol) in 30 ml methyl isobutyl ketone was added 3-bromo-1-propanol (276 mg, 2 mmol). The mixture was refluxed for 48 h, cooled, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1, v/v). Concentration of the appropriate fractions afforded 300 mg (53%) of 3-[1-(1-hydroxyprop-3-yl)-4-piperidinyl]-6-fluoro-1 H-indazole as an oil.

Workup

  1. temperatureThe mixture was refluxed for 48 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography on silica gel 60 eluting with ethyl acetate:methanol (9:1

Sources & evidence

ORD record
ord-1876f237655f4354bef02145b359aee6
Source dataset
uspto-grants-1995_01
Patent number
US05378714

Reaction notes

Loading…