Water → HCID 18738345, compound

HRID 1934368Notes

Reaction equation

HRID 1934368 reaction equation
[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=1[F:15])([CH3:5])[CH3:4].[CH2:17]([OH:20])[C:18]#[CH:19].O>C(N(CC)CC)C.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>[OH:1][CH2:2][C:3]([NH:6][C:7](=[O:16])[C:8]1[CH:13]=[CH:12][C:11]([C:19]#[C:18][CH2:17][OH:20])=[CH:10][C:9]=1[F:15])([CH3:5])[CH3:4]

Participants

7

Reactant 3

HCID 962WaterHCID 7859Propargyl alcoholHCID 22336260HCID 22336260, compound

Product 1

HCID 18738345HCID 18738345, compoundYield 113.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(2-hydroxy-1,1-dimethylethyl)-4-bromo-2-fluorobenzamide (0.29 g, 1.0 mmol) in triethylamine (5 ml), dichlorobis(triphenylphosphine)palladium(II) (0.035 g, 0.05 mmol), copper(I) iodide (0.009 g, 0.05 mmol) and 2-propyn-1-ol (0.085 g, 1.5 mmol) were added and stirred at 50° C. for 3.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and dried over Na2SO4. After the solvent was evaporated under a reduced pressure, the residue was subjected to silica gel chromatography (hexane/ethyl acetate=1/2) to give the title compound (0.30 g, 94%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. customAfter the solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-7b82f3119d8c44f585c03daa44dc1866
Source dataset
uspto-grants-2002_05
Patent number
US06384033B1

Reaction notes

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