3,3-Dimethyl-1-butyne → HCID 57804123, compound

HRID 2102894Notes

Reaction equation

HRID 2102894 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[CH:15]>C(N(CC)CC)C.[Cu]I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]([C:15]#[C:14][C:13]([CH3:17])([CH3:16])[CH3:12])[CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 57804123HCID 57804123, compoundYield 5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

2,6-dichloropyridine-3-carboxylic acid (2.0 g, 10.42 mmol), 3,3-dimethylbut-1-yne (1.4 mL, 11.46 mmol), copper(I) iodide (0.198 g, 1.04 mmol) and bis(triphenylphosphine) palladium(II) chloride (1.46 g, 2.08 mmol) were stirred in 40 mL triethylamine at room temperature for 24 h. The solvent was removed in vacuo and the residue was purified by column chromatography using 10-50% MeOH/EtOAc to furnish 125 mg (5%) of the title compound as an orange solid. m/z=236 (M−1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-90cb2c6084124db9a65d269121de69fe
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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