Cesium fluoride → 2-Cyclopropylpyridine-3-carbaldehyde

HRID 888966Notes

Reaction equation

HRID 888966 reaction equation
Br[C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]1(B(O)O)[CH2:12][CH2:11]1.[F-].[Cs+]>O1CCOCC1>[CH:10]1([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 2760897Cyclopropylboronic acidHCID 47149512-Bromonicotinaldehyde

Product 1

HCID 574409072-Cyclopropylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A 40 mL reaction vial is charged with 3 mL of 1,4-dioxane and a stirbar. Degas with nitrogen for 5 minutes. Next, the vial is charged with 2-bromonicotinaldehyde (645.134 μmoles, 120.000 mg), cyclopropylboronic acid (1.290 mmoles, 110.831 mg), and cesium fluoride (1.935 mmoles, 293.995 mg). The vial is then degassed again with nitrogen. Next, (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (32.257 μmoles, 26.342 mg) is added and the reaction mixture is heated to 100° C. under nitrogen. Upon reaction completion, the mixture is cooled to room temperature, filtered over a pad of diatomaceous earth with ethyl acetate afford the title compound. GCMS (m/z): 146 (M).

Workup

  1. customA 40 mL reaction
  2. customDegas with nitrogen for 5 minutes
  3. customThe vial is then degassed again with nitrogen
  4. customUpon reaction completion
  5. temperaturethe mixture is cooled to room temperature
  6. filtrationfiltered over a pad of diatomaceous earth with ethyl acetate

Sources & evidence

ORD record
ord-1af119cd878c4ec3afd85ba11102f452
Source dataset
uspto-grants-2012_08
Patent number
US08252798B2

Reaction notes

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