Hexane → HCID 13979741, compound

HRID 1907695Notes

Reaction equation

HRID 1907695 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][C:16]=1[O:17][CH3:18].C(=O)([O-])[O-].[Na+].[Na+].CCCCCC>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[C:16]([O:17][CH3:18])[CH:15]=2)=[N:3][CH:4]=1

Participants

9

Reactant 4

HCID 8058HexaneHCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 27347023,4-Dimethoxyphenylboronic acid

Product 1

HCID 13979741HCID 13979741, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a degassed solution of 2,5-dibromopyridine 35 (0.50 g, 2.11 mmol), 3,4-dimethoxyphenylboronic acid 36 (0.50 g, 2.74 mmol) and sodium carbonate (0.67 g, 6.3 mmol) in ethyleneglycol dimethylether (7 mL) and H2O (2 mL) was added tetrakis(triphenylphosphine)-palladium(0) (0.16 g, 0.14 mmol) and the solution was stirred at 75° C. for 18 h. The reaction mixture was filtered, concentrated, diluted with AcOEt, washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography of the residue (eluent: 3:1 hexane:AcOEt) provided title compound 37 (0.47 g, 76% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additiondiluted with AcOEt
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8b1e079f9094a7d8e7d213873616319
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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