Dichloromethane → HCID 10631441, compound

HRID 1069641Notes

Reaction equation

HRID 1069641 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:7]=2[NH:14]C(OC(C)(C)C)=O)=O)[CH2:3][CH2:2]1.[CH2:22](Cl)Cl>FC(F)(F)C(O)=O>[CH:3]1([C:1]2[NH:14][C:7]3[C:6]([CH:4]=2)=[CH:11][C:10]([O:12][CH3:13])=[CH:9][CH:8]=3)[CH2:2][CH2:22]1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 21191890[2-(Tert-butoxycarbonylamino)-5-methoxyphenyl]cyclopropyl ketone

Product 1

HCID 10631441HCID 10631441, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

[2-(tert-Butoxycarbonylamino)-5-methoxyphenyl] cyclopropyl ketone (13 g, 43 mmol) in 250 mL of CH2Cl2 and 25 mL of trifluoroacetic acid was stirred for 4 hours, washed with water, NaHCO3 solution, dried (Na2SO4) and concentrated at reduced pressure. The residue was chromatographed on silica (eluted with a gradient, toluene→20% EtOAc/hexane) to give 4.15 g (49% yield) of 2-cyclopropyl-5-methoxy-1H-indole as an oil.

Workup

  1. washwashed with water, NaHCO3 solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated at reduced pressure
  4. customThe residue was chromatographed on silica (
  5. washeluted with a gradient, toluene

Sources & evidence

ORD record
ord-961ae6e3ac4d4fdca537208760080353
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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