Trifluoroacetic acid → (2-tert-butyl-6-nitro-1H-indol-3-yl)-acetaldehyde

HRID 549383Notes

Reaction equation

HRID 549383 reaction equation
[C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15](OC)[O:16]C)=[CH:11][CH:10]=[C:9]([N+:20]([O-:22])=[O:21])[CH:8]=2)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH2:14][CH:15]=[O:16])=[CH:11][CH:10]=[C:9]([N+:20]([O-:22])=[O:21])[CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 578992342-tert-butyl-3-(2,2-dimethoxy-ethyl)-6-nitro-1H-indole

Product 1

HCID 57899287(2-tert-butyl-6-nitro-1H-indol-3-yl)-acetaldehydeYield 91.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-tert-butyl-3-(2,2-dimethoxy-ethyl)-6-nitro-1H-indole (0.80 g, 2.6 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (5 mL, 50%) at 0° C. and the resulting solution was stirred at room temperature for 6 h. Saturated sodium bicarbonate was added until pH>7. The aqueous layer was extracted with methylene chloride several times. The combined organic layers were dried over sodium sulfate, filtrated, and concentrated in vacuo. The residue was purified via silica gel column chromatography to give the title compound (0.62 g, 91%). LCMS (m/z): 261.0 (M+1).

Workup

  1. extractionThe aqueous layer was extracted with methylene chloride several times
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltrated
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-cf81f38d407240e19865290ee61cab7c
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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