Dimethylformamide → HCID 86595551, compound

HRID 1477401Notes

Reaction equation

HRID 1477401 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH:23]=2)[CH:7]=[CH:8][C:9]=1OS(C(F)(F)F)(=O)=O)([CH3:3])[CH3:2].[CH3:31][N:32](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.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>[C:31]([C:9]1[CH:8]=[CH:7][C:6]([C:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH:23]=2)=[CH:5][C:4]=1[CH:1]([CH3:3])[CH3:2])#[N:32]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 86595552HCID 86595552, compound

Product 1

HCID 86595551HCID 86595551, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 4-(3-isopropyl-4-{[(trifluoromethyl)sulfonyl]oxy}-phenyl)-3,6-dihydropyridine-1(2H)-carboxylate (0.14 g), zinc cyanide (65 mg), and tetrakis(triphenylphosphine)palladium(0) (25.0 mg) in DMF (3.0 mL) was stirred at 100° C. under nitrogen for 4 h. The reaction was cooled down, diluted with water, extracted with diethyl ether. The combined extract was washed with water, brine, dried and concentrated. tert-Butyl 4-(4-cyano-3-isopropylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (85 mg) was isolated by Combiflash. The isolated product was dissolved in a minimum amount of ethyl acetate and 4 N HCl in dioxane (3.0 mL) was added and stirred for 1 h. Diethyl ether (10 mL) was added and the solid was filtered and washed with ether to give the product 2-isopropyl-4-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile hydrochloride (65 mg).

Workup

  1. temperatureThe reaction was cooled down
  2. extractionextracted with diethyl ether
  3. extractionThe combined extract
  4. washwas washed with water, brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7c9a3296e9e4de6aa98df31064cbcdf
Source dataset
uspto-grants-2016_08
Patent number
US09403775B2

Reaction notes

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