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

HRID 1802756Notes

Reaction equation

HRID 1802756 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-36dc2720b5024accbf4a7480d0d80ddb
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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