Pyridine → HCID 22390451, compound

HRID 1071920Notes

Reaction equation

HRID 1071920 reaction equation
[CH2:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[F:11][C:12]([F:26])([F:25])[S:13]([O:16][C:17]1[CH:22]=[CH:21][C:20](Br)=[CH:19][C:18]=1[Cl:24])(=[O:15])=[O:14].N1C=CC=CC=1.C(N(CC)CC)C>ClCCl.[Cu](I)I.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>[F:26][C:12]([F:11])([F:25])[S:13]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C:3]#[C:2][CH2:1][N:4]2[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[CH:19][C:18]=1[Cl:24])(=[O:15])=[O:14]

Participants

8

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 1268882153678-66-32×HCID 22390452HCID 22390452, compound

Product 1

HCID 22390451HCID 22390451, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1.96 g of 1-prop-2-ynylazepane (compound 4.1) are added, under inert atmosphere, to 4 g of 4-bromo-2-chlorophenyl trifluoromethanesulphonate (compound IIIa.1), 0.062 g of copper iodide, 10 ml of pyridine and 20 ml of triethylamine, followed by 0.457 g of the catalyst dichlorobis(triphenylphosphine)palladium. The reaction mixture is heated at the reflux point for 2 hours, the solvents are evaporated off under reduced pressure, and the residue obtained is taken up in dichloromethane, washed in water and dried over magnesium sulphate. After evaporating off the solvents under reduced pressure, the residue obtained is purified by chromatography on a column of silica gel, eluting with an 80/20 cyclohexane/ethyl acetate mixture; m.p.=192° C.

Workup

  1. temperatureThe reaction mixture is heated at the reflux point for 2 hours
  2. customthe solvents are evaporated off under reduced pressure
  3. customthe residue obtained
  4. washwashed in water
  5. dry with materialdried over magnesium sulphate
  6. customAfter evaporating off the solvents under reduced pressure
  7. customthe residue obtained
  8. customis purified by chromatography on a column of silica gel
  9. washeluting with an 80/20 cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-6cffa8718a1348db9d675ca21aefc2a7
Source dataset
uspto-grants-2005_06
Patent number
US06908914B1

Reaction notes

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