Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 18398752, compound

HRID 1018922Notes

Reaction equation

HRID 1018922 reaction equation
CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.[C:18]([O:22][C:23]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH2:34][CH2:35][O:36]C2CCCCO2)=[C:26]1[C:43]1[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[C:45]([C:53]([F:56])([F:55])[F:54])[CH:44]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>C(O)C.[Cl-].[Na+].O>[C:18]([O:22][C:23]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH2:34][CH2:35][OH:36])=[C:26]1[C:43]1[CH:48]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:46]=[C:45]([C:53]([F:56])([F:54])[F:55])[CH:44]=1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 18398758HCID 18398758, compound

Product 1

HCID 18398752HCID 18398752, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

PPTS (95 mg) was added to a stirred solution of 1-tert-butoxycarbonyl-2-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole (2.1 g) in ethanol (50 ml) and warmed to 50° C. for 3 h. The reaction mixture was allowed to cool to room temperature, poured into brine (80 ml) and extracted into diethyl ether. The organic layers were separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to give a clear oil which crystallized on standing (1.67 g). 1H NMR (CDCl3) δ1.23 (s, 9H), 2.79 (t, 2H, J=7.2 Hz), 3.86 (m, 2H), 7.27 (t, 1H, J=7.0 Hz), 7.34 (t, 1H, J=7.0 Hz), 7.60 (d, 1H, J=10.0 Hz), 7.90 (s, 3H), 8.28 (d, 1H, J=10.0 Hz).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted into diethyl ether
  3. customThe organic layers were separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto give a clear oil which
  8. customcrystallized

Sources & evidence

ORD record
ord-f74bdbd926be4583aebe0b9308e1fcce
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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