Dimethylacetamide → HCID 9975231, compound

HRID 966075Notes

Reaction equation

HRID 966075 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C@H:12]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][C@H:13]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:10].C[C:27]([N:29](C)C)=O>C(OCC)(=O)C.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-]#N.[Zn+2].[C-]#N>[C:27]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C@H:12]1[CH2:17][O:16][C:15]([CH3:19])([CH3:18])[O:14][C@H:13]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:10])#[N:29]

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 10046856HCID 10046856, compound

Product 1

HCID 9975231HCID 9975231, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product from Example 19 (355 mg, 0.88 mmol), tetrakis(triphenylphosphine)palladium(0) (102 mg, 10 mol %) and zinc cyanide (103 mg, 0.88 mmol) in dimethylacetamide (8.0 mL) was heated at 80° C. for 8 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (25 mL). The organic layer was washed with water, separated, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to afford 309 mg of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed with water
  3. customseparated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3dd9be4c1ffb4375a1f742c6ec34e733
Source dataset
uspto-grants-2005_10
Patent number
US06951882B2

Reaction notes

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