Monochloramine → 5-Methanesulfonyl-indol-1-ylamine

HRID 2381998Notes

Reaction equation

HRID 2381998 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)(=[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:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([NH2:20])[CH:9]=[CH:8]2)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 25423MonochloramineHCID 149732305-(Methylsulfonyl)-1H-indoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 685555925-Methanesulfonyl-indol-1-ylamineYield 32%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methanesulfonyl-1H-indole (4.1 mmol) and potassium tert-butoxide (8.2 mmol) in DMF (20 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl in ether (41 mL) is added drop-wise for 15 min 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 (3×40 mL). The combined organic layer is washed with water (2×30 mL) and brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with EtOAc and heptane to afford 5-methanesulfonyl-indole-1-ylamine (230 mg, 32%) as a solid. MS: 211 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.08 (s, 3H), 4.94 (br, 2N—H), 6.55 (d, H), 7.34 (m, H), 7.57 (d, H), 7.73 (m, H), 8.21 (m, H).

Workup

  1. customThe reaction mixture is quenched with 10% Na2S2O3 aqueous solution
  2. extractionextracted with ether (3×40 mL)
  3. washThe combined organic layer is washed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with EtOAc and heptane

Sources & evidence

ORD record
ord-f9dca44530b84eaaa590b75ad8230931
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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