Dimethylformamide → HCID 59762326, compound

HRID 40120Notes

Reaction equation

HRID 40120 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]=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)([CH3:8])[CH3:7].CN([CH:24]=[O:25])C>CCOC(C)=O>[CH:6]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH:24]=[O:25])=[CH:15][CH:14]=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 597623802-Isopropyl-6-nitro-1H-indole2×

Product 1

HCID 59762326HCID 59762326, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

POCl3 (0.12 ml, 1.4 mmol) was added dropwise to anhydrous DMF (1.5 ml) at 0° C. under argon. After stirred for 20 min, a solution of 2-isopropyl-6-nitro-1H-indole (Compound 120, 115 mg, 0.56 mmol) in anhydrous DMF (1.5 ml) was added slowly to the above reaction and stirred for 1 h at 0° C. and 2 h at room temperature. The reaction was diluted with EtOAc, washed with H2O and 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.

Workup

  1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-113939e042ae437eb830e7b09358bc95
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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