Methyl iodide → HCID 21460731, compound

HRID 2082533Notes

Reaction equation

HRID 2082533 reaction equation
[H-].[Na+].ClC1C=CC([C:8](=O)[CH2:9][NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:12]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=CC=1.CI.[O:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1.CN(C)C=O>>[Cl:20][C:18]1[CH:17]=[CH:16][C:42]([C:43](=[O:39])[CH2:8][CH2:9][NH:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=3[Cl:20])[N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:12]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:41][CH:40]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21460762HCID 21460762, compoundHCID 21974620tetrahydrofuran N,N-dimethylformamide2×

Product 1

HCID 21460731HCID 21460731, compound

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (160 mg of a 60% dispersion, 4 mmol) in anhydrous tetrahydrofuran/dimethylformamide (3 mL/2:1) and cool to 0° C. under a nitrogen atmosphere. Add 3-[(p-chlorophenacyl)amino]-2-carbethoxy-4,6-dichloro-1-(tert-butyloxycarbonyl)-indole (2 g, 3.9 mmol) in tetrahydrofuran/dimethylformamide (10 mL/2:1) dropwise to the suspension. Stir at 0° C. for 30 minutes. Add methyl iodide (0.137 mL, 2.2 mmol) and stir for 30 minutes at 0° C. Warm the reaction to room temperature and after 4 hours quench with water (20 mL). Extract with ethyl acetate (20 mL), wash with saturated sodium chloride, dry over magnesium sulfate, filter and concentrate in vacuo to yield the title compound.

Workup

  1. temperatureWarm
  2. customthe reaction to room temperature
  3. customafter 4 hours quench with water (20 mL)
  4. extractionExtract with ethyl acetate (20 mL)
  5. washwash with saturated sodium chloride
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-58fe73b6857a401b896bac3eb7393036
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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