2-Propanesulfonyl chloride → HCID 90031740, compound

HRID 624663Notes

Reaction equation

HRID 624663 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:24][CH:25]([S:27](Cl)(=[O:29])=[O:28])[CH3:26]>C1COCC1.[Cl-].[Na+].O>[CH:25]([S:27]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:13])=[O:11])=[CH:2]1)(=[O:29])=[O:28])([CH3:26])[CH3:24]

Participants

6

Reactant 3

HCID 824082-Propanesulfonyl chlorideHCID 589098Methyl indole-3-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 90031740HCID 90031740, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of methyl 1H-indole-3-carboxylate (0.234 g, 1.336 mmol) in THF (6.68 ml) was added sodium bis(trimethylsilyl)amide (2.67 ml, 2.67 mmol) at RT. After 30 min, propane-2-sulfonyl chloride (0.3 ml, 2.67 mmol) was added and the mixture was stirred for 2 h. The reaction mixture was then poured into brine and extracted twice with EtOAc. The combined extracts were filtered through MgSO4 and concentrated to give the title compound as a brown solid, which was used without further purification.

Workup

  1. extractionextracted twice with EtOAc
  2. filtrationThe combined extracts were filtered through MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-644ff3ff06bb497496745becd893f128
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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