p-Toluenesulfonic acid monohydrate → (5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

HRID 2173969Notes

Reaction equation

HRID 2173969 reaction equation
[Cl:1][C:2]1[C:3]([CH2:22][O:23]C2CCCCO2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.CC1C=CC(S(O)(=O)=O)=CC=1.O>CCO>[Cl:1][C:2]1[C:3]([CH2:22][OH:23])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 867015385-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole

Product 1

HCID 86701537(5-Chloro-7-methyl-1-tosyl-1H-indol-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-5-chloro-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole (4.1 g, 9.5 mmol) and TsOH.H2O (359 mg, 1.9 mmol) in EtOH (50 mL) was stirred at room temperature for 21 h. The reaction mixture was concentrated. The mixture was diluted with CH2Cl2. The organic phase was successively washed with 5% aq. NaHCO3, H2O and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, without need of further purification. 1H NMR (400 MHz, ACETONITRILE-d3) δ 7.84 (d, J=3.79 Hz, 1H), 7.59 (d, J=8.34 Hz, 2H), 7.33 (d, J=8.34 Hz, 2H), 7.10 (s, 1H), 7.00 (d, J=3.79 Hz, 1H), 4.84 (d, J=5.81 Hz, 2H), 3.14 (t, J=5.81 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionThe mixture was diluted with CH2Cl2
  3. washThe organic phase was successively washed with 5% aq. NaHCO3, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-329d3019688f4eadacb036c8cc4fe3ee
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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