Water → HCID 69590004, compound

HRID 890164Notes

Reaction equation

HRID 890164 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[C:12]([CH3:20])[NH:11][C:10]([CH3:21])=[C:9]2[C:22]([O:24][CH2:25][CH2:26][C:27]#[N:28])=[O:23])[CH:5]=[CH:6][CH:7]=1.I[C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36][CH2:37][CH2:38][C:39]#[N:40])=[O:35])=[CH:32][CH:31]=1.C(N(CC)CC)C.O>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH:18]=[CH:19][C:30]3[CH:31]=[CH:32][C:33]([C:34]([O:36][CH2:37][CH2:38][C:39]#[N:40])=[O:35])=[CH:41][CH:42]=3)=[O:15])=[C:12]([CH3:20])[NH:11][C:10]([CH3:21])=[C:9]2[C:22]([O:24][CH2:25][CH2:26][C:27]#[N:28])=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 222504052-Cyanoethyl 4-iodobenzoateHCID 69590171HCID 69590171, compound

Product 1

HCID 69590004HCID 69590004, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

307 mg (0.77 mmol) of 5-(2-propene-1-yl) 3-(2-cyanoethyl) 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate, 278 mg (0.92 mmol) of 2-cyanoethyl 4-iodobenzoate, 19 mg(0.08 mmol) of palladium acetate and 0.14 ml (1.0 mmol) of triethylamine were heated at 100° C. under stirring in 5 ml of DMF overnight. Water was added to the reaction mixture. After the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1) to obtain the title compound.

Workup

  1. extractionAfter the extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-74f5db127eaa42898f49e40d60a784b8
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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