Monochloramine → 6-Methanesulfonyl-indole-1-ylamine

HRID 2382000Notes

Reaction equation

HRID 2382000 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CC(C)([O-])C.[K+].[NH2:20]Cl>CN(C=O)C.CCOCC>[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2[NH2:20])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 25423MonochloramineHCID 27610676-methanesulfonyl-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 685531846-Methanesulfonyl-indole-1-ylamineYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methanesulfonyl-1H-indole (2.66 mmol) and potassium tert-butoxide (5.32 mmol) in DMF (15 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl in ether (26.6 mL) is added drop-wise for 15 minutes at rt and the reaction mixture is stirred at rt for 2 h. The reaction mixture is quenched with 10% Na2S2O3 aqueous solution, and extracted with ether (3×20 mL). The combined organic layer is washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is triturated with EtOAc to give 6-methanesulfonyl-indole-1-ylamine (270 mg, 51%) as a solid. MS: 211 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.09 (s, 3H), 6.49 (d, H), 7.41 (m, H), 7.61 (d, H), 7.71 (d, H), 8.12 (s, H).

Workup

  1. customThe reaction mixture is quenched with 10% Na2S2O3 aqueous solution
  2. extractionextracted with ether (3×20 mL)
  3. washThe combined organic layer is washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with EtOAc

Sources & evidence

ORD record
ord-c969d854a07344358ab3c83ed2459684
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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