3,3-Dimethyl-1-butyne → 2-{2-[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-ethanesulfonylamino}-5-methyl-benzenesulfonamide

HRID 2283352Notes

Reaction equation

HRID 2283352 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[S:21]([NH2:24])(=[O:23])=[O:22])(=[O:12])=[O:11])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:34][C:35]([CH3:39])([CH3:38])[C:36]#[CH:37]>CN(C)C=O.C(OCC)(=O)C.[Cu]I.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:34][C:35]([CH3:39])([CH3:38])[C:36]#[C:37][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=2[S:21]([NH2:24])(=[O:23])=[O:22])(=[O:12])=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 135123,3-Dimethyl-1-butyneHCID 81531DiisopropylethylamineHCID 577509642-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide

Product 1

HCID 577509262-{2-[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-ethanesulfonylamino}-5-methyl-benzenesulfonamideYield 25.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[2-(4-bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide (0.08 g, 0.18 mmol), N,N-diisopropylethylamine (0.1 mL, 0.55 mmol), and copper(I) iodide (7 mg, 0.04 mmol) in anhydrous N,N-dimethylformamide (2 mL) was degassed with nitrogen for 30 min. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14 mg, 0.02 mmol) and 3,3-dimethyl-1-butyne (0.045 mL, 0.37 mmol) were added and the reaction mixture was heated in a sealed tube at 80° C. overnight. The reaction mixture was diluted with ethyl acetate (20 mL), washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC, using 5% methanol in dichloromethane as the eluent, to give 20 mg (25% yield) of the title compound.

Workup

  1. additionwere added
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-c64f3222e86a43f8ac9ccac19f7c0cbc
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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