Triethylamine → 5-Bromo-2-methylfuro[2,3-b]pyridine

HRID 2047023Notes

Reaction equation

HRID 2047023 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:10][CH2:11][CH2:12]C[N+](CCCC)(CCCC)CCCC.[F-].C(N(CC)CC)C>[Pd].C1(C)C=CC=CC=1.ClCCl.[Cu](I)I>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:11]([CH3:12])[O:8][C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 178517595HCID 178517595, compound

Product 1

HCID 667356905-Bromo-2-methylfuro[2,3-b]pyridine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 83717Copper iodideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-bromo-3-iodopyridin-2-ol (1 equiv), copper iodide (3 equiv), palladium catalyst (0.05 equiv), TBAF (1 equiv), triethylamine (3.3 equiv) and alkyne (1 equiv) in toluene was stirred at room temperature until the reaction was deemed complete by TLC analysis. The reaction mixture was diluted with dichloromethane, washed with water, saturated sodium bicarbonate, and brine, dried over sodium bicarbonate, filtered through celite, concentrated, and purified on silica gel to give the product, 5-bromo-2-methylfuro[2,3-b]pyridine.

Workup

  1. washwashed with water, saturated sodium bicarbonate, and brine
  2. dry with materialdried over sodium bicarbonate
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. custompurified on silica gel

Sources & evidence

ORD record
ord-1a047f12269e49daa2d6add5317e1e9f
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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