Triethylamine → HCID 66940522, compound

HRID 1367917Notes

Reaction equation

HRID 1367917 reaction equation
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=1.C(N(CC)CC)C>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.CN(C=O)C>[C:1]1([C:7]#[C:8][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([OH:18])=[O:17])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 7351504-Bromopyridine-2-carboxylic acid

Product 1

HCID 66940522HCID 66940522, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.728 mL (6.5 mmol) of phenyl acetylene was added to a mixture of 10.1 g (5 mmol) of 4-bromopicolinic acid, 91 mg (0.13 mmol) of dichlorobis(triphenylphosphine)-palladium(II), 29 mg (0.15 mmol) of copper(I) iodide, 10 mL of triethylamine and 2 mL of DMF and heated at 80° C. overnight. The reaction mixture was filtered. The filtrate was concentrated and partitioned between 5 mL of 2 N Na2CO3 solution, 25 mL of water and 30 mL of ether. The aqueous layer was separated and washed again with ether (30 mL). 10% aq. HCl was added to adjust the pH to 5. The aqueous layer was extracted with dichloromethane (2×50 mL), and the combined organic layers were dried over sodium sulfate. Evaporation of the solvents in vacuo gave 1.028 g (4.61 mmol, 92%) of 4-phenylethynyl-pyridine-2-carboxylic acid. LCMS: 224 (M+1)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. custompartitioned between 5 mL of 2 N Na2CO3 solution, 25 mL of water and 30 mL of ether
  4. customThe aqueous layer was separated
  5. washwashed again with ether (30 mL)
  6. addition10% aq. HCl was added
  7. extractionThe aqueous layer was extracted with dichloromethane (2×50 mL)
  8. dry with materialthe combined organic layers were dried over sodium sulfate
  9. customEvaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-23d7f82e6ab1493a9d40baa7b3044bd2
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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