1-Ethynyl-3-fluorobenzene → Adx 10059

HRID 1271571Notes

Reaction equation

HRID 1271571 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]([F: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>[F: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 5202181-Ethynyl-3-fluorobenzeneHCID 20493073-Amino-2-bromo-4,6-dimethylpyridine

Product 1

HCID 10331863Adx 10059Yield 72%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of Cul (41 mg, 0.2 mmol) in triethylamine (12 ml) were added 2-bromo-4,6-dimethyl-pyridin-3-ylamine (870 mg, 4.33 mmol), (PPh3)2PdCl2 (152 mg, 0.22 mmol), and 1-ethynyl-3-fluorobenzene (500 μl, 4.33 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 745 mg (3.10 mmol, 72%) of (2-(3-fluoro-phenylethynyl)-4,6-dimethyl-pyridin-3-yl)amine as a brown solid.

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-6c098e5333af479e8fa86f557b97bc63
Source dataset
uspto-grants-2007_04
Patent number
US07205411B2

Reaction notes

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