Water → HCID 69589195, compound

HRID 1244980Notes

Reaction equation

HRID 1244980 reaction equation
C(OP([CH2:9][C:10]#[N:11])(OCC)=O)C.[H-].[Na+].[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[NH:22][CH:23]=[C:24]([CH:32]=O)[C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:17][CH:16]=1.O>O1CCCC1>[F:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[NH:22][CH:23]=[C:24]([CH:32]=[CH:9][C:10]#[N:11])[C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 219226862-(4-Fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrrole

Product 1

HCID 69589195HCID 69589195, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.92 ml (18.02 mmol) of diethylphosphonoacetonitrile were added to 16 ml of tetrahydrofuran and the resulting solution was added to a suspension of 786 mg (18.02 mmol) of 55% sodium hydride in 60 ml of tetrahydrofuran with ice-cooling, and the resulting mixture was then stirred at room temperature for 1.5 hours. At the end of this time, a suspension of 4.00 g (15.02 mmol) of 2-(4-fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in step (iii) above] in 30 ml of tetrahydrofuran was added to this mixture and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure to afford a solid which was washed with diethyl ether to give 2.94 g (yield 68%) of the title compound as a pale brown powder.

Workup

  1. temperaturecooling
  2. additionwas added to this mixture
  3. stirringthe resulting mixture was stirred at room temperature for 1 hour
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customto afford a solid which
  10. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-98e7d09c291444fb82f5aecc7ec449f0
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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