Methyl iodide → HCID 68717433, compound

HRID 1159796Notes

Reaction equation

HRID 1159796 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[C:14]([CH:19]=[CH2:20])[CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[CH3:22]C([N-]C(C)C)C.IC>CO>[CH3:22][C:11]1[N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[C:18]2[C:13]([CH:12]=1)=[C:14]([CH:19]=[CH2:20])[CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 10401571HCID 10401571, compound2×

Product 1

HCID 68717433HCID 68717433, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Phenylsulfonyl)-4-vinyl-1H-indole (190 mg, 0.7 mmol, Intermediate 45) was weight in to a pre dried reaction flask and purged with nitrogen gas for 1 h. Dry THF (50 mL) was added and the reaction flask was cooled to −78° C. before LDA (0.35 mL, 0.7 mmol, 2M) was added. The reaction was stirred for 15 minutes before iodomethane (95.2 mg, 0.7 mmol) was added. Allowed the reaction mixture to slowly reach RT ON. Added 1 mL MeOH and evaporated the reaction mixture on silica. Purified by flash chromatography using 20% DCM in hexanes. Got 61 mg of a white solid, 30% yield. MS (ESI+) for C17H15NO2S m/z 298 (M+H)+.

Workup

  1. customdried
  2. customreaction flask
  3. custompurged with nitrogen gas for 1 h
  4. additionDry THF (50 mL) was added
  5. additionwas added
  6. additionwas added
  7. customto slowly reach RT
  8. customevaporated the reaction mixture on silica
  9. customPurified by flash chromatography

Sources & evidence

ORD record
ord-6d67b8cfc1874f1ca76b7a633f1675b4
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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