Triethylamine → HCID 57827174, compound

HRID 1842229Notes

Reaction equation

HRID 1842229 reaction equation
[CH2:1]([O:4][CH3:5])[C:2]#[CH:3].C(N(CC)CC)C.Br[C:14]1[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[N:18][CH:19]=1>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu](I)I>[CH3:5][O:4][CH2:1][C:2]#[C:3][C:14]1[CH:15]=[CH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[N:18][CH:19]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 57827174HCID 57827174, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bis(triphenylphosphine)palladium (II) chloride (82.4 mg), copper iodide (22.3 mg), methyl propargyl ether (828 μL) and triethylamine (1.9 mL) were added to a solution of methyl 5-bromo-pyridine-2-carboxylate (423 mg) in tetrahydrofuran (10.6 mL), and the mixture was stirred at room temperature for 19 hours and 50 minutes. The reaction solution was concentrated under reduced pressure and water was added to the residue. After extraction with ethyl acetate, the organic layer was washed with brine and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (88.1 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure and water
  2. additionwas added to the residue
  3. extractionAfter extraction with ethyl acetate
  4. washthe organic layer was washed with brine
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-50cac8e3fde44fc9826014c675f43824
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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