Monochloramine → 5-Fluoro-1H-indol-1-amine

HRID 2381990Notes

Reaction equation

HRID 2381990 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.CC(C)([O-])C.[K+].[NH2:17]Cl>CN(C=O)C.CCOCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([NH2:17])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 25423MonochloramineHCID 678615-FluoroindoleHCID 23665647Potassium tert-butoxide

Product 1

HCID 450786905-Fluoro-1H-indol-1-amineYield 30%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-fluoro-1H-indole (16.9 mmol) and potassium tert-butoxide (33.8 mmol) in DMF (76 mL) is stirred at rt under N2 for 2 h. 0.15 M NH2Cl. in ether (169.2 mL) is added drop-wise for 15 minutes at rt. The reaction mixture is stirred at rt for 2 h, then quenched with 10% Na2S2O3 aqueous solution and extracted with ether. The organic layer is separated, dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60-80% EtOAc in heptane to afford 5-fluoro-indole-1-ylamine (751 mg, 30%) as a solid. 1H NMR (300 MHz, CDCl3): δ 4.80 (br, 2N—H), 6.38 (d, H), 7.00 (m, H), 7.19-7.43 (m, 3H).

Workup

  1. customquenched with 10% Na2S2O3 aqueous solution
  2. extractionextracted with ether
  3. customThe organic layer is separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 60-80% EtOAc in heptane

Sources & evidence

ORD record
ord-7528a26af1f64844a35fe469d5d38fea
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…