5-Bromo-2-methoxypyridine → HCID 58790345, compound

HRID 418744Notes

Reaction equation

HRID 418744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.Br[C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[N:29][CH:30]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:25]3[CH:30]=[N:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[S:10][C:3]=12

Participants

4

Reactant 2

HCID 27348955-Bromo-2-methoxypyridineHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 58790345HCID 58790345, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tributyltin derivative 6 (2.00 g, 4.36 mmol) (scheme 91) in toluene (10 mL) was added Ph(PPh3)4 (0.503 g, 0.436 mmol) followed by 5-bromo-2-methoxypyridine (0.62 mL, 4.8 mmol). Nitrogen gas was bubbled directly into the reaction mixture for 30 minutes before it was heated to reflux for 16 h. The reaction mixture was then cooled to room temperature and the yellow precipitate was collected by filtration and washed with hexanes. The material was then further purified by flash chromatography (eluent 20 to 50% ethyl acetate in hexanes) to afford the titled compound 418 as a fluffy white solid (0.752 g, 62% yield). MS (m/z): 277.0 (M+H).

Workup

  1. customNitrogen gas was bubbled directly into the reaction mixture for 30 minutes before it
  2. temperaturewas heated
  3. temperatureto reflux for 16 h
  4. filtrationthe yellow precipitate was collected by filtration
  5. washwashed with hexanes
  6. customThe material was then further purified by flash chromatography (eluent 20 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-eafd0170d8b74cfa9bd9d01f7a8e9fe7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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