Dimethylformamide → Ethyl3-Formyl-2-isopropyl-1H-indole-6-carboxylate

HRID 40060Notes

Reaction equation

HRID 40060 reaction equation
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=2)([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl.CN([CH:26]=[O:27])C>>[CH:26]([C:12]1[C:11]2[C:6](=[CH:7][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=2)[NH:5][C:4]=1[CH:1]([CH3:3])[CH3:2])=[O:27]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 59762345Ethyl2-Isopropyl-1H-indole-6-carboxylate2×

Product 1

HCID 59762423Ethyl3-Formyl-2-isopropyl-1H-indole-6-carboxylate

Conditions

Temperature
25 °C

Procedure

To a solution of ethyl 2-isopropyl-1H-indole-6-carboxylate (Compound 33, 2.00 g, 8.66 mmol) in DMF (12 ml) at 0° C. under argon then added dropwise POCl3 (1.58 ml, 17.3 mmol) was added dropwise. The reaction was stirred for 30 minutes at 25° C. then cooled to 0° C., quenched with saturated NaHCO3, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound as a light tan solid.

Workup

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C.
  3. customquenched with saturated NaHCO3
  4. additiondiluted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-3d7cd3c0fcc74d7cb5299da3226f7c16
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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