Sulfuric Acid → HCID 66835035, compound

HRID 61838Notes

Reaction equation

HRID 61838 reaction equation
[O:1]1[CH:5]2[CH2:6][O:7][CH2:8][CH:4]2[O:3]S1(=O)=O.[Br:11][C:12]1[CH:24]=[C:23]2[C:15]([C:16]3[C:17](=[O:32])[C:18]4[CH:30]=[CH:29][C:28](O)=[CH:27][C:19]=4[C:20]([CH3:26])([CH3:25])[C:21]=3[NH:22]2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].S(=O)(=O)(O)O>CN(C=O)C.O.C1COCC1>[Br:11][C:12]1[CH:24]=[C:23]2[C:15]([C:16]3[C:17](=[O:32])[C:18]4[CH:30]=[CH:29][C:28]([O:3][CH:4]5[CH:5]([OH:1])[CH2:6][O:7][CH2:8]5)=[CH:27][C:19]=4[C:20]([CH3:25])([CH3:26])[C:21]=3[NH:22]2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 10796Cesium carbonateHCID 11228993Tetrahydro-furo[3,4-d][1,3,2]dioxathiol 2,2-dioxideHCID 66834244HCID 66834244, compound

Product 1

HCID 66835035HCID 66835035, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen atmosphere, tetrahydro-furo[3,4-d][1,3,2]dioxathiol 2,2-dioxide (71.5 mg, 0.420 mmol) was dissolved in DMF (1.40 mL), added with 3-bromo-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound A5-1, 50.0 mg, 0.140 mmol) and cesium carbonate (228 mg, 0.700 mmol), and stirred at 80° C. for 15 hr. Subsequently, sulfuric acid (0.10 mL, 18 M), THF (3.00 mL) and water (0.50 mL) were added to the mixture, which was then stirred at room temperature for 24 hr and further at 60° C. for 24 hr. The reaction solution was added to water, extracted with ethyl acetate, washed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine, and dried over sodium sulfate. After filtering and concentration under reduced pressure, the resulting residues were washed with dichloromethane and purified by NH silica gel column chromatography (ethyl acetate/THF) to obtain the target compound (44.7 mg, 72%).

Workup

  1. stirringwas then stirred at room temperature for 24 hr and further at 60° C. for 24 hr
  2. extractionextracted with ethyl acetate
  3. washwashed with water, saturated aqueous solution of sodium bicarbonate, and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtering
  6. concentrationconcentration under reduced pressure
  7. washthe resulting residues were washed with dichloromethane
  8. custompurified by NH silica gel column chromatography (ethyl acetate/THF)

Sources & evidence

ORD record
ord-bb9de65967204b27ac77d02d8b58e523
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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