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

HRID 402816

Reaction equation

HRID 402816 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 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (558 mg, 1.71 mmol) was added to a stirred room temperature of 6-methoxy-1H-indole-3-carbaldehyde (100 mg, 0.57 mmol) in DMF (1.0 mL) and the mixture was stirred at room temperature for 15 minutes. Then 2-iodopropane (0.114 mL, 1.14 mmol) was added and the solution was stirred for 80° C. for 2 hours. The solution was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (2×15 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 crude title intermediate (108 mg).

Workup

  1. stirringthe solution was stirred for 80° C. for 2 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate (2×15 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-659b8288bf354e9297588a86b7d09714
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Linked notes

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