Propargyl alcohol → (Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide

HRID 2211664Notes

Reaction equation

HRID 2211664 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12](Br)[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([OH:21])[C:19]#[CH:20]>[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:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:20]#[C:19][CH2:18][OH:21])[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 21961437[(3-Bromo-4-fluorophenyl)methyl]-carbamic acid tert-butyl ester

Product 1

HCID 131725909(Tert-butoxy)-n-{[4-fluoro-3-(3-hydroxyprop-1-ynyl)phenyl]methyl}carboxamide

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butoxy-N-[(3-bromo-4-fluorophenyl)methyl]carboxamide (0.6 g, 2.0 mmol, Step A), CuI (38 mg, 0.2 mmol), PdCl2(PPh3)2 (72 mg, 0.1 mmol), propargyl alcohol (0.35 mL, 6.0 mmol) and TEA (12 mL) was heated at 100° C. for 5 h. The resulting mixture was filtered, and the filtrate was concentrated. The residue was purified by SiO2 chromatography to give the title compound. MS (ES+): 297 (M+NH4)+. Calc'd C15H22FN2O3-297.34.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-467be4e71881463fa5aad2e5640c0d28
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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