Water → HCID 66696592, compound

HRID 1672563Notes

Reaction equation

HRID 1672563 reaction equation
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:4])#[C-:2].[Br:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=1[F:24].C([O-])([O-])=O.[K+].[K+].O>CO.[N+](C(S(C1C=CC(C)=CC=1)(=O)=O)C)#[C-]>[Br:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]2[O:21][CH:2]=[N:1][C:3]=2[CH3:4])=[CH:18][C:17]=1[F:24]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27834114-Bromo-3-fluorobenzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696592HCID 66696592, compoundYield 91.1%

Reagents, catalysts & solvents 2

HCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.67 g, 7.97 mmol), 4-bromo-3-fluorobenzaldehyde (1.62 g, 7.97 mmol), and K2CO3 (2.20 g, 15.9 mmol) in MeOH (40 mL) was heated to reflux. After 1.5 hr additional 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (106 mg, 0.51 mmol) was added and the reaction mixture was again heated at reflux for 1.5 hr. The reaction was cooled to ambient temperature, water (200 mL) was added and the product was extracted with EtOAc (200 mL). The organic layer was washed with brine and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF25-40G column, 0%-30% EtOAc/hexanes, 30 mL/min), which yielded 1.86 g (91%) of the title compound as an orange solid. 1H NMR (300 MHz, CH3OH-d4) δ 8.18 (s, 1H), 7.73 (dd, J=8.4, 7.3 1H), 7.49 (dd, J=9.9, 2.0 1H), 7.41 (dd, J=8.3, 1.8 1H), 2.42 (s, 3H). MS (DCI+) m/z 256/258 (M+H).

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction mixture was again heated
  3. temperatureat reflux for 1.5 hr
  4. extractionthe product was extracted with EtOAc (200 mL)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel (Analogix® SF25-40G column, 0%-30% EtOAc/hexanes, 30 mL/min), which

Sources & evidence

ORD record
ord-3d6bb6c2c355459b93a9c5cbc74c0ca8
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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