Methyl 1-butyl-4-iodo-1H-indole-6-carboxylate → Methyl 1-butyl-4-cyano-1H-indole-6-carboxylate

HRID 348971

Reaction equation

HRID 348971 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9](I)[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cu][C:20]#[N:21]>CN1C(=O)CCC1>[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:20]#[N:21])[CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 21086136Methyl 1-butyl-4-iodo-1H-indole-6-carboxylateHCID 178418546HCID 178418546, compound

Product 1

HCID 21086135Methyl 1-butyl-4-cyano-1H-indole-6-carboxylateYield 47.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of methyl 1-butyl-4-iodo-1H-indole-6-carboxylate (EXAMPLE SP-218, Step 4) (1.47 g) in N-methyl pyrrolidinone (15 mL) was added copper (I) cyanide (1.1 g). The mixture was heated to 150° C. for 6 h, removed from heat and cooled to room temperature. The mixture was partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 20% ethyl acetate as eluent to give 0.5 g of the title compound: 1H NMR (CDCl3) δ 0.955, 1.32, 1.85, 3.98, 4.23, 6.76, 7.43, 8.16, 8.30.

Workup

  1. customremoved
  2. temperaturefrom heat
  3. temperaturecooled to room temperature
  4. customThe mixture was partitioned between water and ethyl acetate
  5. customthe layers were separated
  6. washThe organic layer was washed three times with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee21cadc60b044f99f29ecd9e72965a7
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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