1-Chloro-3-ethynylbenzene → (2-(3-Chloro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amine

HRID 1271572Notes

Reaction equation

HRID 1271572 reaction equation
Br[C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)#[CH:12]>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>[Cl:19][C:15]1[CH:14]=[C:13]([C:11]#[C:12][C:2]2[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 1230861-Chloro-3-ethynylbenzeneHCID 20493073-Amino-2-bromo-4,6-dimethylpyridine

Product 1

HCID 10467628(2-(3-Chloro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amineYield 25%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of Cul (5.7 mg, 30 μmol) in triethylamine (1.6 ml) were added 2-bromo-4,6-dimethyl-pyridin-3-ylamine (120 mg, 0.60 mmol, described in Example 12), (PPh3)2PdCl2 (21 mg, 30 μmol), and 1-ethynyl-3-chlorobenzene (98 mg, 0.72 mmol). The reaction mixture was stirred for 30 min. at room temperature and for 3 h under reflux. The solvent was evaporated and the crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 4:1) to yield 39 mg (0.15 mmol, 25%) of (2-(3-chloro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amine as a brown oil.

Workup

  1. temperatureunder reflux
  2. customThe solvent was evaporated
  3. customthe crude residue was purified by flash chromatography (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-d54fa21eee414f17a4771c51392a5984
Source dataset
uspto-grants-2007_04
Patent number
US07205411B2

Reaction notes

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