Methyl iodide → HCID 71090093, compound

HRID 331040Notes

Reaction equation

HRID 331040 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Cl:11])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([Cl:11])=[CH:7][N:8]2[CH3:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 122699216-bromo-3-chloro-1H-indole

Product 1

HCID 71090093HCID 71090093, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromo-3-chloro-1H-indole (D72) (894 mg, 3.88 mmol) in DMF (16 mL) was cooled to 0° C. under an atmosphere of nitrogen. Sodium hydride (60% in mineral oil) (163 mg, 4.07 mmol) was added portionwise followed by methyl iodide (0.243 mL, 3.88 mmol). The mixture was stirred for 1.5 hour, slowly allowing to warm to RT. The mixture was quenched with saturated aq. NH4Cl and extracted with ethyl acetate (2×150 mL). The organic extracts were combined, dried with anhydrous sodium sulfate, filtered and evaporated to dryness. The residues were purified on silica, eluting with cyclohexane and ethyl acetate (0-50%). The appropriate fractions were combined and evaporated to dryness to give title compound (831 mg). LCMS (A): m/z (M−H)− 242/244, C9H7BrClN requires 243/245 (acidic).

Workup

  1. customThe mixture was quenched with saturated aq. NH4Cl
  2. extractionextracted with ethyl acetate (2×150 mL)
  3. dry with materialdried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residues were purified on silica
  7. washeluting with cyclohexane and ethyl acetate (0-50%)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5d6cf19456ba4b38918de7416d77005e
Source dataset
uspto-grants-2014_11
Patent number
US08877742B2

Reaction notes

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