Potassium Carbonate → HCID 66696634, compound

HRID 1672592Notes

Reaction equation

HRID 1672592 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[N+:10]([CH:12](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:13])#[C-:11].C([O-])([O-])=O.[K+].[K+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH:11]=[N:10][C:12]=2[CH3:13])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98775625-Bromopyridine-2-carbaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696634HCID 66696634, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-bromopicolinaldehyde (7.80 g, 41.9 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (8.78 g, 41.9 mmol), and K2CO3 (7.53 g, 54.5 mmol) in MeOH (150 mL) was heated at reflux for 3 hr. The reaction was then cooled to room temperature, the MeOH was evaporated at reduced pressure, and the crude material was partitioned between EtOAc and water. The separated aqueous layer was extracted twice with EtOAc. The combined organic extract was washed twice with water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel (Analogix® SF65-600 column, 0% to 50% EtOAc/hexane) to afford 7.32 g (73%) of the title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 8.78 (dd, J=2.4, 0.6, 1H), 8.44 (s, 1H), 8.15 (dd, J=8.5, 2.4, 1H), 7.64 (dd, J=8.5, 0.6, 1H), 2.50 (s, 3H). MS (DCI+) m/z 239/241 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hr
  3. customthe MeOH was evaporated at reduced pressure
  4. customthe crude material was partitioned between EtOAc and water
  5. extractionThe separated aqueous layer was extracted twice with EtOAc
  6. extractionThe combined organic extract
  7. washwas washed twice with water
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude material was chromatographed on silica gel (Analogix® SF65-600 column, 0% to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-a73a4d5f5378473b8331c1363a19e09a
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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