Ethanol → 2-(2,5-Dimethylpyrrolyl)-6-(4-fluoro-naphth-1-yl)pyridine

HRID 322049Notes

Reaction equation

HRID 322049 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](B(O)O)=[CH:4][CH:3]=1.[CH3:15][C:16]1[NH:17][C:18]([CH3:28])=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[CH3:15][C:16]1[NH:17][C:18]([CH3:28])=[CH:19][C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([F:1])=[CH:3][CH:4]=2)[N:22]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27826754-Fluoro-1-naphthaleneboronic Acid (contains varying amounts of Anhydride)HCID 543198942-(2,5-Dimethylpyrrolyl)-6-bromopyridine

Product 1

HCID 543666152-(2,5-Dimethylpyrrolyl)-6-(4-fluoro-naphth-1-yl)pyridineYield 700.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 50 mL round-bottomed flask equipped with condenser and N2 inlet were added 404 mg (2.13 mmol) 4-fluoronaphthalene-1-boronic acid, 534 mg (2.13 mmol) 2-(2,5-dimethylpyrrolyl)-6-bromopyridine, 902 mg (8.51 mmol) sodium carbonate, 150 mg tetrakistriphenylphosphine, 10 mL ethanol, and 2 mL water. The reaction was refluxed overnight, cooled, poured into water, and extracted into ethyl acetate. After combining with another run on a larger scale, the combined organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford 4.72 g (85%) of an oil. 1H-NMR (δ, CDCl3): 2.25 (s, 6H), 5.92 (s, 2H), 7.1-7.2 (m, 2H), 7.4-7.6 (m, 4H), 7.95 (t, J=8, 1H), 8.12 (d, J=8, 1H), 8.19 (d, J=8, 1H); 13C-NMR (δ, CDCl3): 13.41, 106.97, 108.82, 109.02, 120.18, 120.78, 120.84, 123.42, 123.81, 123.96, 125.48, 126.20, 127.32, 127.68, 127.76, 128.56, 132.35, 133.90, 138.22, 151.87, 157.82, 158.30, 160.34; MS (%): 317 (parent+1, 100); HRMS Calculated. for C21H18N2F (parent+1): 317.1454, Found: 317.1462.

Workup

  1. customTo a 50 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed overnight
  3. temperaturecooled
  4. extractionextracted into ethyl acetate
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2566db8aa68744779ba1f228028756e0
Source dataset
uspto-grants-2001_04
Patent number
US06211208B1

Reaction notes

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