2-Methyl-3-butyn-2-ol → HCID 19605481, compound

HRID 1603573Notes

Reaction equation

HRID 1603573 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.[CH3:23][C:24]([OH:28])([C:26]#[CH:27])[CH3:25]>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>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:3]=[C:2]([C:27]#[C:26][C:24]([CH3:25])([OH:28])[CH3:23])[CH:7]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 69186894-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine

Product 1

HCID 19605481HCID 19605481, compoundYield 52%

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, 93 mg (1.1 mmole) 2-methyl-3-butyn-2-ol, 38 mg copper(I)-iodide and 35 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 1 hour in 5 ml dimethylformamide and 5 ml diethylamine. 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. Flash chromatography (silicagel, hexane/ethyl acetate 7/3 ) and recrystallisation of the residue from ethanol yields 200 mg (52%) pure 4-[4-(4-amino-benzenesulfonyl)-6-pyrrolidine-1-yl-pyridine-2-yl]-2-methyl-but-3-yn-2-ol als a white solid mp.: 168-170° C.

Workup

  1. customThe solvents are removed
  2. additionthe residue is diluted with dichloromethane
  3. washThe dichloromethane solution is washed twice with water
  4. dry with materialdried over magnesiumsulfate
  5. concentrationconcentrated in vacuo
  6. customFlash chromatography (silicagel, hexane/ethyl acetate 7/3 ) and recrystallisation of the residue from ethanol

Sources & evidence

ORD record
ord-57a54eeadcc54449942b54f0e668feca
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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