Potassium Carbonate → HCID 66718393, compound

HRID 2096706Notes

Reaction equation

HRID 2096706 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+]>[Cu]I.O1CCOCC1>[OH:9][CH2:8][C:6]1[N:7]=[C:2]([N:7]2[CH2:6][CH2:5][CH2:4][C:10]2=[O:13])[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 3517811(6-Bromopyridin-2-yl)methanol

Product 1

HCID 66718393HCID 66718393, compoundYield 204.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (6-bromopyridine-2-methanol (9.76 g, 51.9 mmol), copper(I) iodide (0.99 g, 5.19 mmol) N,N′-dimethylethane-1,2-diamine (1.12 mL, 10.38 mmol), 1,4-dioxane (400 mL) and potassium carbonate (14.35 g, 103.84 mmol) was heated at reflux for 8 h, cooled, concentrated in vacuo and partitioned between EtOAc and water. The organic phase was separated, the aqueous phase re-extracted with EtOAc and the combined organic extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (10.19 g, quantitative) as a pale-yellow solid; NMR δH (400 MHz, CDCl3) 8.32 (1H, d, J 8.5 Hz), 7.69 (1H, dd, J 8.5, 7.5 Hz), 6.96 (1H, dd, J 7.5, 1.5 Hz), 4.71 (2H, d, J 5.0 Hz), 4.17-4.13 (2H, m), 3.50 (1H, t, J 5.0 Hz), 2.70-2.66 (2H, m), 2.19-2.11 (2H, m); (M+H)+ 193; LC-MS Retention time 1.46 min.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. custompartitioned between EtOAc and water
  6. customThe organic phase was separated
  7. extractionthe aqueous phase re-extracted with EtOAc
  8. dry with materialthe combined organic extracts were dried (MgSO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35d6d27837bc422689014908290580a4
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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