Dimethylformamide → HCID 13383890, compound

HRID 420816Notes

Reaction equation

HRID 420816 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:8])[CH3:7].CN([CH:21]=[O:22])C>CCOC(C)=O>[CH:6]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH:21]=[O:22])=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 873072-Isopropyl-1H-indole2×

Product 1

HCID 13383890HCID 13383890, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

POCl3 (0.86 ml, 9.4 mmol) was added dropwise to anhydrous DMF (4 ml) at 0° C. with stirring. After 30 min, this solution was added dropwise to a solution of 2-isopropyl-1H-indole (Compound 38, 1.24 g, 7.8 mmol) in DMF (16 ml) at 0° C. under argon. The reaction was stirred for 1 h while it warmed up to room temperature. The reaction was diluted with EtOAc, washed with aq. NaHCO3, brine, dried over Na2SO4, and concentrated in vacuo. The residual solid was washed with Et2O to yield 2-isopropyl-1H-indole-3-carbaldehyde (Compound 39) as a beige solid.

Workup

  1. stirringThe reaction was stirred for 1 h while it
  2. washwashed with aq. NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with Et2O

Sources & evidence

ORD record
ord-96aec4465b694a6d9142b168f3f585e7
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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