Benzenesulfonyl chloride → HCID 86703272, compound

HRID 2409947Notes

Reaction equation

HRID 2409947 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[C:37]1([S:43](Cl)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Cl-].[NH4+]>CN(C)C=O>[C:37]1([S:43]([N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:45])=[O:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86703271HCID 86703271, compound

Product 1

HCID 86703272HCID 86703272, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (3.04 g) in N,N-dimethylformamide (34 mL) was added sodium hydride (50 to 72% in oil, 342 mg) in one portion under ice-cooling. This mixture was stirred for 30 minutes under ice-cooling. Then, benzenesulfonyl chloride (1.04 mL) was added dropwise thereto, followed by stirring at room temperature for 4.5 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (1.10 g). 1H-NMR (CDCl3) δ ppm: 3.92 (3H, s), 4.09 (2H, s), 5.44 (2H, s), 6.62-6.68 (1H, m), 6.80 (1H, dd, J=2.4, 8.6 Hz), 7.21 (1H, d, J=8.6 Hz), 7.24-7.53 (16H, m), 7.85-7.93 (2H, m).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 4.5 hours
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine successively
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-962fd050027542af89ff38ce22949c6e
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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