Dimethylformamide → HCID 45257889, compound

HRID 1873462Notes

Reaction equation

HRID 1873462 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][C:11]([C:18]3[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[CH2:12][N:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(OCC)(=O)C.[CH3:32][N:33](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:20]1[CH:19]=[C:18]([C:11]2([C:14]([F:17])([F:16])[F:15])[CH2:10][C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([CH:3]=3)[C:32]#[N:33])=[N:13][CH2:12]2)[CH:23]=[C:22]([Cl:24])[CH:21]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 45257781HCID 45257781, compound

Product 1

HCID 45257889HCID 45257889, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

5-(3-Bromo-4-fluorophenyl)-3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole (0.88 g) was dissolved in DMF (10 ml), and the solution was deaerated and then left to stand in an argon atmosphere. To the reaction mixture, Zn(CN)2 (0.45 g) and Pd(PPh3)4 (0.67 g) were added. The mixture was stirred for 4 hours at 90° C. The reaction mixture was returned to room temperature, and then ethyl acetate was added thereto. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, and then dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 5-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-fluorobenzonitrile (0.25 g) at a yield of 32%.

Workup

  1. waitleft
  2. customwas returned to room temperature
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering the reaction mixture
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c4923baad2994e33a9357ff9cbc32893
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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