Phenylacetylene → HCID 19605522, compound

HRID 1603574Notes

Reaction equation

HRID 1603574 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=1.[C:23]1([C:29]#[CH:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O.C(NCC)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:23]1([C:29]#[C:30][C:2]2[CH:7]=[C:6]([S:8]([C:11]3[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=3)(=[O:10])=[O:9])[CH:5]=[C:4]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 2

HCID 10821PhenylacetyleneHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 19605522HCID 19605522, compoundYield 64.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8021DiethylamineSolvent

Procedure

A mixture of 382 mg (1 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 112 mg (1.1 mmole) phenylacetylene, 38 mg copper(I)-iodide and 35 mg bis(triphenylphosphine)-palladium(II)-chloride in 5 ml dimethylformamide and 5 ml diethylamine is refluxed for 2 hours. The solvents are removed and the residue is diluted with dichloromethane. The dichloromethane solution is washed twice with water, dried over magnesiumsulfate and concentrated in vacuo. Recrystallisation of the residue from chloroform/ethanol yields 260 mg (64%) pure 4-(2-phenylethynyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine als a pale yellow solid mp.: 202-204° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. customThe solvents are removed
  3. additionthe residue is diluted with dichloromethane
  4. washThe dichloromethane solution is washed twice with water
  5. dry with materialdried over magnesiumsulfate
  6. concentrationconcentrated in vacuo
  7. customRecrystallisation of the residue from chloroform/ethanol

Sources & evidence

ORD record
ord-af5f623bf2494902ad7d90afdc584c4d
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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