Methanesulfonyl chloride → methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate

HRID 715957Notes

Reaction equation

HRID 715957 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][CH2:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH:18]=1>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][CH2:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:23]([O-:25])=[O:24])=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH:18]=1)(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 70983888methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate2×

Product 1

HCID 86712115methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylateYield 99.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

Methanesulfonyl chloride (0.176 g) was added to a solution of methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate (Intermediate 21, 0.360 g) in pyridine (1 mL) and DCM (10 mL) and the reaction mixture was stirred at room temperature for 4 hours. The mixture was diluted with DCM, washed with aqueous citric acid (5%), aqueous sodium bicarbonate and brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in toluene and evaporated to dryness, four times to give methyl 2-(3-methanesulfonyloxypropyl)-5-nitro-1H-indole-4-carboxylate (0.460 g) as an orange gum.

Workup

  1. washwashed with aqueous citric acid (5%), aqueous sodium bicarbonate and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in toluene
  6. customevaporated to dryness, four times

Sources & evidence

ORD record
ord-acc6923098c046a89520401d6a440795
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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