Dimethylcarbamoyl Chloride → 5-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide

HRID 1971416Notes

Reaction equation

HRID 1971416 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:12]=[CH:11][N:10]([CH3:13])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li]CCCC.CCCCCC.[CH3:25][N:26]([CH3:30])[C:27](Cl)=[O:28]>C1COCC1>[CH3:25][N:26]([CH3:30])[C:27]([C:11]1[N:10]([CH3:13])[N:9]=[C:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])[CH:12]=1)=[O:28]

Participants

6

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8058HexaneHCID 132489953-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 593947615-(2,5-Dimethyl-pyrrol-1-yl)-2-methyl-2H-pyrazole-3-carboxylic acid dimethylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2,5-dimethyl-pyrrol-1-yl)-1-methyl-1H-pyrazole (2.0 g, 11.4 mmol) in THF (100 mL) at −78° C., 2.5M nBuLi in Hexane (5.5 mL, 13.7 mmol) is added. After stirring for 1.5 hour dimethylcarbamyl chloride (1.26 mL, 13.7 mmol) is added. After 10 min the ice bath is removed and the reaction allowed to reach room temperature and stir at room temperature for 2 hour before being poured into water, separated, and the water layer extracted with DCM. The organic layers are combined and concentrated. The residue is purified by FCC to give the title compound. MS (ESI) m/z 247.2 (M+1).

Workup

  1. additionis added
  2. customAfter 10 min the ice bath is removed
  3. customto reach room temperature
  4. additionbefore being poured into water
  5. customseparated
  6. extractionthe water layer extracted with DCM
  7. concentrationconcentrated
  8. customThe residue is purified by FCC

Sources & evidence

ORD record
ord-1d2b32cbcca045bb911b36d305008226
Source dataset
uspto-grants-2013_04
Patent number
US08431584B2

Reaction notes

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