Chloroiodomethane → HCID 59430661, compound

HRID 506113Notes

Reaction equation

HRID 506113 reaction equation
[CH2:1]([Zn]CC)C.[CH2:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH:18]=[CH2:19])[CH:15]=2)[C:10]([C:20]#[N:21])=[CH:9]1)[CH3:7].ClCI.[NH4+].[Cl-].[OH-].[NH4+]>C(OCC)(=O)C.ClCCCl>[CH:18]1([O:17][C:14]2[CH:15]=[C:16]3[C:11]([C:10]([C:20]#[N:21])=[CH:9][N:8]3[CH2:6][CH3:7])=[CH:12][CH:13]=2)[CH2:1][CH2:19]1

Participants

8

Reactant 5

HCID 11644ChloroiodomethaneHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 59430695HCID 59430695, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59430661HCID 59430661, compoundYield 45.7%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

Via a syringe, diethyl zinc is added to a mixture of 1-ethyl-6-vinyloxy-1H-indole-3-carbonitrile (288.1 mg, 1.36 mmol), chloroiodomethane (268.9 mg, 1.53 mmol) and 5 ml of 1,2-dichloroethane over a period of 10 min, maintaining the temperature at −10° C. The mixture is warmed to 20-25° C. for 20 min., and then cooled back to 0° C. Saturated NH4Cl (15 mL), concentrated ammonium hydroxide (15 mL), and ethyl acetate (15 mL) are added in sequence at this temperature, and stirred for 10 min. After the phases are separated, the aqueous phase is back-extracted with ethyl acetate (10 mL). The combined organic phases are washed with saturated NH4Cl (10 mL), dried over MgSO4 and then the solution is concentrated and the product is purified by chromatography, eluting with 15-30% ethyl acetate/hexanes to afford 140.5 mg (45.7% yield) of 6-cyclopropoxy-1-ethyl-1H-indole-3-carbonitrile as a yellow solid.

Workup

  1. temperatureThe mixture is warmed to 20-25° C. for 20 min.
  2. temperaturecooled back to 0° C
  3. customAfter the phases are separated
  4. extractionthe aqueous phase is back-extracted with ethyl acetate (10 mL)
  5. washThe combined organic phases are washed with saturated NH4Cl (10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationthe solution is concentrated
  8. customthe product is purified by chromatography
  9. washeluting with 15-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ecbfe9bf12804e898431ffa2f9da8c9c
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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