Potassium Hydroxide → HCID 11712061, compound

HRID 1988205Notes

Reaction equation

HRID 1988205 reaction equation
[OH-].[K+].[CH:3]1([C:6]([CH:14]2[CH2:16][CH2:15]2)([C:8]2[S:9][C:10]([SH:13])=[N:11][N:12]=2)[OH:7])[CH2:5][CH2:4]1.Br[C:18]1[CH:27]=[C:26]2[C:21]([C:22]([C:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][C:24](=[O:28])[O:25]2)=[CH:20][CH:19]=1>CO>[CH:14]1([C:6]([CH:3]2[CH2:5][CH2:4]2)([OH:7])[C:8]2[S:9][C:10]([S:13][C:18]3[CH:27]=[C:26]4[C:21]([C:22]([C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)=[CH:23][C:24](=[O:28])[O:25]4)=[CH:20][CH:19]=3)=[N:11][N:12]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 233702367-Bromo-4-(pyridin-3-yl)-2H-1-benzopyran-2-oneHCID 178520018HCID 178520018, compound

Product 1

HCID 11712061HCID 11712061, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

KOH (0.089 g, 1.59 mmol) was added to a solution of dicyclopropyl(5-mercapto-1,3,4-thiadiazol-2-yl)methanol (0.363 g, 1.60 mmol) in dry MeOH. When a solution was obtained, the reaction mixture was concentrated to dryness. Dry toluene was then added and the mixture was concentrated to dryness again. The residue was dissolved in NMP, 7-bromo-4-pyridin-3-yl-2H-chromen-2-one (400 mg, 1.32 mmol) was added and the resulting mixture was stirred at 120° C. for 16 h. The reaction mixture was cooled and partitioned between aqueous NH4OAc and EtOAc. The organic phase was washed with brine, dried over anhydrous Na2SO4, concentrated and purified on silica gel column (toluene-acetone, 90:10 to 70:30) to give the title compound. 1H NMR (400 MHz, CDCl3): δ 8.82 (d, 1H), 8.72 (s,1H), 7.81 (dt, 1H), 7.64 (s, 1H), 7.58-7.50 (m, 1H), 7.48-7.41 (m, 2H), 6.46 (s, 1H), 2.57 (s, 1H), 1.40-1.31 (m, 2H), 0.69-0.57 (m, 6H), 0.50-0.44 (m, 1H).

Workup

  1. customWhen a solution was obtained
  2. concentrationthe reaction mixture was concentrated to dryness
  3. additionDry toluene was then added
  4. concentrationthe mixture was concentrated to dryness again
  5. dissolutionThe residue was dissolved in NMP
  6. temperatureThe reaction mixture was cooled
  7. custompartitioned between aqueous NH4OAc and EtOAc
  8. washThe organic phase was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated
  11. custompurified on silica gel column (toluene-acetone, 90:10 to 70:30)

Sources & evidence

ORD record
ord-7e68e81e8e2349f48e35e86ae4e10d44
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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