3,3-Dimethyl-1-butyne → HCID 69063586, compound

HRID 2102899Notes

Reaction equation

HRID 2102899 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[CH:15]>[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.C(N(CC)CC)C>[CH3:12][C:13]([CH3:17])([CH3:16])[C:14]#[C:15][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 135123,3-Dimethyl-1-butyneHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 69063586HCID 69063586, compoundYield 92.5%

Reagents, catalysts & solvents 3

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

Procedure

To a 250 mL sealed reaction vessel was added methyl 5-bromopyridine-2-carboxylate (5 g, 23 mmol), copper(I) iodide (0.43 g, 2.3 mmol), bis(triphenylphosphine) palladium(II) chloride (3.23 g, 4.6 mmol), and triethylamine (80 mL). The mixture was allowed to stir for approximately 10 minutes upon which 3,3-dimethylbut-1-yne (2.83 g, 34.5 mmol) was added. The tube was sealed, stirred at room temperature overnight, and heated at 60° C. for one hour. The mixture was allowed to cool, and then concentrated under vacuum to a residue. The residue was purified by column chromatography on silica gel using EtOAc/hexanes (1:10) as eluent to give the product (4.62 g, 92%) as a tan solid which was used directly in the next step.

Workup

  1. customTo a 250 mL sealed
  2. customreaction vessel
  3. additionwas added
  4. customThe tube was sealed
  5. temperatureheated at 60° C. for one hour
  6. temperatureto cool
  7. concentrationconcentrated under vacuum to a residue
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-85d21d62bf964aedb6d1da488b7246de
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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