Isopropyl iodide → 6-methoxy-1-(propan-2-yl)-1H-indole-3-carbaldehyde

HRID 402814

Reaction equation

HRID 402814 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][NH:15]2)=[CH:11][CH:10]=1.I[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]=[O:19])=[CH:14][N:15]2[CH:21]([CH3:23])[CH3:22])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

Product 1

HCID 772301786-methoxy-1-(propan-2-yl)-1H-indole-3-carbaldehydeYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Cesium carbonate (577 mg, 1.77 mmol) was added to a stirred room temperature solution of 6-methoxy-1H-indole-3-carbaldehyde (104 mg, 0.590 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes when 2-iodopropane (0.118 mg, 1.181 mmol) was added. The solution was stirred at 80° C. for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate (2×20 mL) and saturated sodium bicarbonate (5 mL), washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated to give the title intermediate (120 mg).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (2×20 mL) and saturated sodium bicarbonate (5 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c88445f42e054bc6a22df31aca2f613d
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Linked notes

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