Isopropyl iodide → 5-Bromo-1-(1-methylethyl)-1H-indole-3-carboxaldehyde

HRID 402818Notes

Reaction equation

HRID 402818 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH:17]=[O:18].I[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:20]([CH3:22])[CH3:21])[CH:12]=[C:11]2[CH:17]=[O:18]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 701375-Bromoindole-3-carbaldehyde

Product 1

HCID 50503775-Bromo-1-(1-methylethyl)-1H-indole-3-carboxaldehydeYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (545 mg, 1.67 mmol) was added to a stirred room temperature of 5-bromo-1H-indole-3-carbaldehyde (125 mg, 0.56 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes. Then 2-iodopropane (0.112 mL, 1.116 mmol) was added and 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 under reduced pressure to give the title compound (148 mg).

Workup

  1. stirringthe solution was stirred at 80° C. for 2 hours
  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 under reduced pressure

Sources & evidence

ORD record
ord-5275eaa72e7746c7ac144dfe63438bab
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

Loading…