Methyl iodide → HCID 22220128, compound

HRID 1793873Notes

Reaction equation

HRID 1793873 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH3:21]C(C)([O-])C.[K+].C1COCC1.IC>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:21])[CH:6]=[C:5]2[S:11]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 22220124HCID 22220124, compoundHCID 66863523KOtBu THF

Product 1

HCID 22220128HCID 22220128, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-bromo-3-(4-fluoro-benzenesulfonyl)-1H-indole (0.315 g, 0.89 mmole) in tetrahydrofuran (4 mL) was added 1M potassium t-butoxide/THF (1.0 mL, 1.0 mmol). After 10 minutes iodomethane (0.16 g, 1.1 mmole) was added. The reaction mixture was stirred at room temperature overnight and then passed through a pad of silica gel (230–400 mesh) eluting with 50% ethyl acetate/hexane. The eluate was concentrated under reduced pressure to provide a residue that was crystallized from ethanol/hexanes to give 0.3 g of 5-Bromo-3-(4-fluoro-benzenesulfonyl)-1-methyl-1H-indole.

Workup

  1. washeluting with 50% ethyl acetate/hexane
  2. concentrationThe eluate was concentrated under reduced pressure
  3. customto provide a residue that
  4. customwas crystallized from ethanol/hexanes

Sources & evidence

ORD record
ord-5c3d1dba330b492a861ce692d4d5d575
Source dataset
uspto-grants-2006_04
Patent number
US07022708B2

Reaction notes

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