Hydrazine → HCID 67417340, compound

HRID 383723Notes

Reaction equation

HRID 383723 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([F:16])[CH:11]=1)[C:5](=O)[CH:6]([CH3:8])[CH3:7].[NH2:18]N>CO.CCOC(C)=O>[F:16][C:12]1[CH:11]=[C:10]([C:4]2[CH:3]=[N:2][NH:18][C:5]=2[CH:6]([CH3:8])[CH3:7])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 67416039HCID 67416039, compound

Product 1

HCID 67417340HCID 67417340, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-dimethylamino-2-(2-fluoro-pyridin-4-yl)-4-methyl-pent-1-en-3-one (crude, 26.5 mmol) in methanol (50 mL) is added hydrazine (0.84 mL, 26.5 mmol) at 0° C. The reaction mixture is stirred for 4 h, diluted with EtOAc, and washed with water. The organic layer is washed with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography (SiO2, EtOAc/heptan 5:1) afforded 3.8 g of 2-fluoro-4-(5-isopropyl-1H-pyrazol-4-yl)-pyridine as a white solid.

Workup

  1. washwashed with water
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, EtOAc/heptan 5:1)

Sources & evidence

ORD record
ord-5553adc89f344754b70c122a53ddfdcd
Source dataset
uspto-grants-2013_02
Patent number
US08367687B2

Reaction notes

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