Ammonia → HCID 66880696, compound

HRID 1893553Notes

Reaction equation

HRID 1893553 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[CH:10]=[C:9](Br)[CH:8]=1)[CH3:2].N.[CH3:25][N:26](C)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>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[CH:10]=[C:9]([C:25]#[N:26])[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 66881239HCID 66881239, compound

Product 1

HCID 66880696HCID 66880696, compoundYield 37%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To N,N-dimethylformamide (50 ml) were added the compound (6.04 g, 15.6 mmol) obtained in step C, zinc cyanide (1.84 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.61 g, 3.12 mmol), and the mixture was stirred with heating at 100° C. for 5 hr. The reaction mixture was cooled to room temperature, diluted aqueous ammonia was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (1.91 g, yield 37%) as a pale-bistered solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe solution was concentrated under reduced pressure
  7. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-82d27fe8b707498db51dcc0333716fc9
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

Loading…