Phenylacetylene → HCID 10081793, compound

HRID 1271555Notes

Reaction equation

HRID 1271555 reaction equation
Br[C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]1([C:16]#[CH:17])[CH:15]=[CH:14][CH:13]=[CH:12][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>[CH3:9][C:4]1[N:3]=[C:2]([C:17]#[C:16][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([NH2:8])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 10821PhenylacetyleneHCID 144180512-Bromo-6-methylpyridin-3-amine

Product 1

HCID 10081793HCID 10081793, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Cul (10 mg, 50 μmol) in triethylamine (5 ml) were added (2-bromo-6-methyl-pyridin-3-yl)amine (200 mg, 1.07 mmol) and (PPh3)2PdCl2 (36 mg, 50 μmol). The reaction mixture was cooled to 0° C. and phenylacetylene (176 μl, 1.60 mmol) was added. The reaction mixture was allowed to warm to room temperature and then heated under reflux for 14 h. The solvent was evaporated and the crude residue was purified by flash chromatography (hexane/ethyl acetate 4:1) to yield 105 mg (0.50 mmol, 47%) of (6-methyl-2-phenylethynyl-pyridin-3-yl)amine as a yellow solid.

Workup

  1. temperatureto warm to room temperature
  2. temperatureheated
  3. temperatureunder reflux for 14 h
  4. customThe solvent was evaporated
  5. customthe crude residue was purified by flash chromatography (hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-81b9e49a1c2945198317f08fde98948e
Source dataset
uspto-grants-2007_04
Patent number
US07205411B2

Reaction notes

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