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Methyl iodide → 2-Methyl-5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indole

HRID 2102031
Notes
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Reaction equation

HRID 2102031 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH2:28]CCC.CI>C1COCC1>[CH3:28][C:13]1[N:14]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])[C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[CH:17][CH:16]=2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 118246245-(Phenylmethoxy)-1-phenylsulfonylindoleHCID 178418339Butyllithium

Product 1

HCID 578002872-Methyl-5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indoleYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 5-[(phenylmethyl)oxy]-1-(phenylsulfonyl)-1H-indole (1.6 g, 4.4 mmol, synthesized as described in Example 22A) in THF (10 mL), under N2, at −78° C., was added n-BuLi (2.5 M solution in hexanes, 2.15 mL, 5.37 mmol) dropwise. After stirring at −78° C. for 30 min, methyl iodide (0.94 g, 6.6 mmol) was added. After 30 min, the −78° C. bath was removed. The solution was warmed to rt. 5% HCl (10 mL) was then added and the mixture was partitioned between EtOAc and water. The organic phase was washed with water and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (20-70% EtOAc-hexanes gradient) to afford the title compound (0.8 g, 77% yield): MS (ES) m/z 478 (M+1).

Workup

  1. waitAfter 30 min
  2. customthe −78° C. bath was removed
  3. temperatureThe solution was warmed to rt
  4. addition5% HCl (10 mL) was then added
  5. customthe mixture was partitioned between EtOAc and water
  6. washThe organic phase was washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (20-70% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-758f7daec50f4d3285df7ce3c7ba926d
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572820B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes