1-Butyne → HCID 21193314, compound

HRID 1068455Notes

Reaction equation

HRID 1068455 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1.[CH:12]#[C:13][CH2:14][CH3:15]>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.C(N(CC)CC)C>[C:12]([C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1)#[C:13][CH2:14][CH3:15]

Participants

6

Reactant 2

HCID 78461-ButyneHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 21193314HCID 21193314, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2-chloropyridine-4-carboxylate (3.32 g, 19.3 mmol), bis(triphenylphosphine)palladium(II) chloride (0.82 g, 1.1 mmol), copper(I) iodide (0.36 g, 1.9 mmol), triethylamine (30 mL), and n-but-1-yne (˜5 g) was heated in a sealed tube at 80° C. overnight. The product mixture was concentrated, and the residue was subjected to column chromatography on silica gel eluting with chloroform. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. concentrationThe product mixture was concentrated
  2. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-78cb0fad0b48497abf837031443014a5
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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