Propargyl alcohol → Isohexane ethyl acetate

HRID 1444043Notes

Reaction equation

HRID 1444043 reaction equation
Br[C:2]1[N:3]=[C:4]([O:28][CH3:29])[C:5]([N:8](COCC[Si](C)(C)C)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[CH2:30]([OH:33])[C:31]#[CH:32].[CH2:34](N([CH2:39][CH3:40])CC)C>[Cu]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>[C:30]([O:33][CH2:39][CH3:40])(=[O:10])[CH3:31].[CH3:12][CH2:17][CH2:16][CH:15]([CH3:14])[CH3:34].[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[C:4]([O:28][CH3:29])=[N:3][C:2]([C:32]#[C:31][CH2:30][OH:33])=[CH:7][N:6]=1)(=[O:10])=[O:11]

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 59168156N-(5-Bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide

Product 2

HCID 21882781Isohexane ethyl acetateHCID 591681002,3-Dichloro-N-[5-(3-hydroxy-1-propynyl)-3-methoxy-2-pyrazinyl]benzenesulphonamide

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Procedure

A mixture of N-(5-bromo-3-methoxy-2-pyrazinyl)-2,3-dichloro-N-[{2-(trimethylsilanyl)ethoxy}methyl]benzenesulphonamide (Example 55a) (0.52 g), propargyl alcohol (0.223 mL), copper(I)iodide (0.05 g) and bis(triphenylphosphine)palladium(II) chloride (0.1 g) in triethylamine (3 mL) was stirred at room temperature and under nitrogen for 16 h. The solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound containing the SEM ([2-(trimethylsilyl)ethoxy]methyl) protecting group (0.38 g). 0.074 g of this compound was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (2 mL). After 1 h the solvent was evaporated. Chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the title compound (0.043 g).

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d71187e891654376be20771b673cd87e
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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