Methanesulfonyl chloride → Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate

HRID 348960

Reaction equation

HRID 348960 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:15][S:16]([NH:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 14243967Methyl 4-amino-1H-indole-6-carboxylate

Product 1

HCID 21086208Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylateYield 50.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of methyl 4-amino-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added 4-dimethylaminopyridine (1.46 g) and methanesulfonyl chloride (0.6 g). The mixture was heated to 60° C. for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 0.71 g of the title compound: 1H NMR (CDCl3) δ 3.02, 3.94, 6.69, 7.42, 7.81, 8.04.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bbf755d5c106475a89061efcce26d471
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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