2-(Tributylstannyl)pyridine → HCID 66844763, compound

HRID 1696312Notes

Reaction equation

HRID 1696312 reaction equation
Br[C:2]1[C:3]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C([Sn](CCCC)(CCCC)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC>CN(C=O)C>[CH:13]1([O:12][C:3]2[C:2]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][N:4]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 66844699Methyl 5-bromo-6-(cyclopentyloxy)nicotinate

Product 1

HCID 66844763HCID 66844763, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 5-bromo-6-(cyclopentyloxy)nicotinate (4.53 g, 15.1 mmol) and 2-(tributylstannyl)pyridine (5.00 g, 13.6 mmol) was stirred in 100 mL of DMF at 120° C. for 6 h. The resulting solution was cooled and concentrated in vacuo. The crude reaction mixture was then partitioned between EtOAc and water. The layers were separated and the aqueous layer was extracted 1×EtOAc. The organic phases were combined, washed 3× brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was taken up in CH2Cl2 and loaded on to a 40 g pre-packed silica gel column. Elution with 0-30% EtOAc:hexanes provided the title compound as an off-white powder (1.71 g, 38%). MS m/z: 299 (M+1).

Workup

  1. temperatureThe resulting solution was cooled
  2. concentrationconcentrated in vacuo
  3. customThe crude reaction mixture
  4. customwas then partitioned between EtOAc and water
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted 1×EtOAc
  7. washwashed 3× brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. washElution with 0-30% EtOAc

Sources & evidence

ORD record
ord-287d97deeb02447b837d4221287ea2e7
Source dataset
uspto-grants-2012_04
Patent number
US08163766B2

Reaction notes

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