Triethylamine → HCID 22180661, compound

HRID 1795859Notes

Reaction equation

HRID 1795859 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[N:6][CH:7]=1.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#[CH:18].C(N(CC)CC)C>CN(C=O)C.CCOC(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.[Cu]I>[C:19]1([C:17]#[C:18][C:2]2[CH:3]=[CH:4][C:5]([S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)(=[O:10])=[O:9])=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 22180670HCID 22180670, compound

Product 1

HCID 22180661HCID 22180661, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 5-bromo-2-(phenylsulfonyl)pyridine (6.00 g), ethynylbenzene (2.87 mL), dichlorobis(triphenylphosphine)palladium (II) (140 mg) and CuI (38 mg) in DMF (90 mL) was added triethylamine (8.42 mL) and the mixture was stirred at 60° C. for 1 h. The reaction mixture was diluted with EtOAc, washed with water and brine, dried over sodium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (CHCl3 to CHCl3-EtOAc 10:1) to give 5-(phenylethynyl)-2-(phenylsulfonyl)pyridine (6.33 g) as a solid.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (CHCl3 to CHCl3-EtOAc 10:1)

Sources & evidence

ORD record
ord-a00a153fcc4848eeaaf33c979066d62e
Source dataset
uspto-grants-2006_04
Patent number
US07030121B2

Reaction notes

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