Sulfuric Acid → HCID 11514254, compound

HRID 1009536Notes

Reaction equation

HRID 1009536 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](=[N:16][OH:17])[CH3:15])=[CH:4]1)[CH3:2].[Li][CH2:19]CCC.CN(C=O)C.OS(O)(=O)=O>C1COCC1.O>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]2[CH:15]=[CH:19][O:17][N:16]=2)=[CH:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6228DimethylformamideHCID 72295607HCID 72295607, compoundHCID 178418339Butyllithium

Product 1

HCID 11514254HCID 11514254, compoundYield 12.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

1-(1-Ethyl-6-methoxy-1-H-indole-3-yl)ethanone oxime (100 mg, 0.43 mmol) is dissolved in THF (900 μL) at 0° C. n-BuLi (450 μL, 2.5 M in hexanes, 1.12 mol) is added dropwise, resulting in instant precipitation of solids. DMF (70 μL, 0.9 mol) in 260 μL, of THF is then added dropwise. This is stirred at 0° C. for 1 h, then at room temperature for 1 h. The reaction mixture is pipetted into a mixture containing 1 mL of H2O, 1 mL of THF, and 100 μL, of concentrated H2SO4. This mixture is heated at 75° C. for 1 h and then is partitioned between H2O and EtOAc. The organic phase is dried and concentrated. Purification by column chromatography (CH2Cl2) yields 1-ethyl-3-isoxazol-3-yl-6-methoxy-1-H-indole product as a white solid (13 mg, 12%).

Workup

  1. additionis added dropwise
  2. customresulting in instant precipitation of solids
  3. waitat room temperature for 1 h
  4. temperatureThis mixture is heated at 75° C. for 1 h
  5. customis partitioned between H2O and EtOAc
  6. customThe organic phase is dried
  7. concentrationconcentrated
  8. customPurification by column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-7ce99151bd90466bbf996c96ecef70a2
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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