Dimethylformamide → 1-Benzyl-2-isopropyl-6-methoxy-1H-indole-3-carbaldehyde

HRID 40032Notes

Reaction equation

HRID 40032 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[CH:15]=[C:14]1[CH:24]([CH3:26])[CH3:25])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN([CH:30]=[O:31])C>CCOC(C)=O>[CH2:6]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([O:22][CH3:23])[CH:20]=2)[C:15]([CH:30]=[O:31])=[C:14]1[CH:24]([CH3:26])[CH3:25])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 597624051-Benzyl-2-isopropyl-6-methoxy-1H-indole2×

Product 1

HCID 597623941-Benzyl-2-isopropyl-6-methoxy-1H-indole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

POCl3 (0.48 ml, 5.23 mmol) was added dropwise to anhydrous DMF (2 ml) at 0° C. under argon. After stirred for 30 min, this solution was added dropwise to a solution of 1-benzyl-2-isopropyl-6-methoxy-1H-indole (Compound 4, 583 mg, 2.09 mmol) in anhydrous DMF (8 ml) at 0° C. under argon. The reaction was stirred for 1 h at 0° C. and 30 min at room temperature, diluted with EtOAc, washed with aqueous NaHCO3, brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as a light yellow syrup.

Workup

  1. stirringThe reaction was stirred for 1 h at 0° C. and 30 min at room temperature
  2. washwashed with aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-c18d13e281454ad6b34ba010b43c80b3
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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