Ethanol → HCID 53936797, compound

HRID 1977901Notes

Reaction equation

HRID 1977901 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.[CH3:10][C:11]1[NH:12][C:13]([CH3:29])=[CH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)[N:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[CH3:10][C:11]1[NH:12][C:13]([CH3:29])=[CH:14][C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:27]=[CH:26][C:25]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:24][CH:23]=2)[N:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 54347025HCID 54347025, compound

Product 1

HCID 53936797HCID 53936797, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 271 mg (2.20 mmol) 3-pyridylboronic acid (Rec. Trav. Chim., 93, 21 (1974)), 720 mg (2.20 mmol) 2-(2,5-dimethylpyrrolyl)-6-(4-bromophenyl)-pyridine, 933 mg (8.81 mmol) sodium carbonate, 128 mg (0.110 mmol) tetrakistriphenylphosphine palladium, 9 mL ethanol, and 1 mL water. The mixture was refluxed 20 hours 100 mg 3-pyridiylboronic acid added, and refluxing continued for 2 hours. The reaction was then cooled, poured into water and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride as eluant to afford the product as an oil, 350 mg (49%).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. additionadded
  3. temperaturerefluxing
  4. temperatureThe reaction was then cooled
  5. extractionextracted into ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ccb707ce8caf40c8a9e388cab7af1f85
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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