Borane → HCID 68854758, compound

HRID 1984691Notes

Reaction equation

HRID 1984691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([C:14](O)=[O:15])=[N:9]2)=[CH:4][CH:3]=1.B>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([CH2:14][OH:15])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 35813371-(4-fluorophenyl)-5-methyl-1H-1,2,4-triazole-3-carboxylic acid

Product 1

HCID 68854758HCID 68854758, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-(4-fluoro-phenyl)-5-methyl-1H-[1,2,4]triazole-3-carboxylic acid (may be prepared in analogy to DE3525205, 1986, 10.7 g, 48.4 mmol) in THF (50 mL) was added borane (1 M in THF, 121 mL, 121 mmol) and the resulting suspension was heated to reflux for 1 h. After concentration and extraction with aqueous sodium hydrogencarbonate and ethyl acetate the combined organic layers were washed with brine and dried over sodium sulfate. Concentration and purification by chromatography (SiO2, hexane:ethyl acetate=100:0 to 33:67) afforded the title compound (4.60 g, 46%) as a white solid. MS: m/e=208.4 [M+H]+.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureto reflux for 1 h
  3. concentrationAfter concentration and extraction with aqueous sodium hydrogencarbonate and ethyl acetate the combined organic layers
  4. washwere washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration and purification by chromatography (SiO2, hexane:ethyl acetate=100:0 to 33:67)

Sources & evidence

ORD record
ord-5f14978bc9c2480ca73d98390b800a8d
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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