Ammonia → HCID 19895588, compound

HRID 1073934Notes

Reaction equation

HRID 1073934 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]3[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=3[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=2)=[N:6][CH:7]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([Sn](C)(C)C)=[CH:24][CH:23]=1.[Cl-].[Li+].N>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:32][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:13]4[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=4[O:11][C:10]([CH3:21])([CH3:20])[CH:9]=3)=[N:6][CH:7]=2)=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 433294Lithium ChlorideHCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 19895603HCID 19895603, compound

Product 1

HCID 19895588HCID 19895588, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

440 mg of 4-(5-iodo-2-pyridyl)-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile, 386 mg of p-tolyltrimethyltin, 144 mg of lithium chloride and 16 mg of bis(triphenylphosphine)palladium dichloride in 4 ml of dimethylformamide were heated at 100° C. for 2 hours. After cooling to room temperature 10% aqueous ammonia and ethyl acetate were added, the phases were separated and the aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution to give 268 mg of 4-[5-(4-methylphenyl)-2-pyridyl]-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile which was used without further purification.

Workup

  1. additionwere added
  2. customthe phases were separated
  3. extractionthe aqueous phase was back-extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-fba1bd7a2cb14fac813ec0152e91ea8b
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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