Benzenesulfonyl chloride → HCID 58914739, compound

HRID 1297782Notes

Reaction equation

HRID 1297782 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si](C(C)(C)C)(C)C)=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40])(C)(C)C.C1COCC1.[H-].[Na+].[C:50]1([S:56](Cl)(=[O:58])=[O:57])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(OCC)(=O)C.CCCCCC>[C:50]1([S:56]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:10]3[CH:11]=[C:12]([CH3:13])[C:7]([OH:6])=[C:8]([CH3:40])[CH:9]=3)([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[C:26]([CH3:39])[CH:25]=3)[C:15]2=[O:23])(=[O:58])=[O:57])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58914719HCID 58914719, compound

Product 1

HCID 58914739HCID 58914739, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

In a 40-mL vial, combine 0.15 g (1.0 mmol) of 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one with 15 mL of dry THF under nitrogen. Add 1.0 equivalent of sodium hydride and stir the resulting mixture 30 minutes under nitrogen. Add 2.0 equivalence of benzenesulfonyl chloride and stir an additional 30 minutes. Remove solvent in vacuuo and chromatograph the crude intermediate (1-Benzenesulfonyl-3,3-bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one) using 1:4 ethyl acetate/hexane to elute. Dissolve the intermediate in refluxing 1:1 THF/methanol and add excess cesium fluoride. Stir for 10 minutes, remove solvent in vacuuo, and add 10 mL of water. Extract with ethyl acetate to obtain 0.06 g (47%) of the titled compound as an off-white solid: LCMS (system 2) tR=4.05 min (100%), ESMS (M+1) m/z=514.2; 1H NMR (DMSO-d6); 8.28 (s, 1H), 7.98 (d, 2H), 7.90 (d, 1H), 7.81 (t, 1H), 7.65 (t, 2H), 7.39 (m, 1H), 7.20 (m, 2H), 6.30 (s, 4H), 1.93 (s, 12H).

Workup

  1. stirringstir an additional 30 minutes
  2. washto elute
  3. dissolutionDissolve the intermediate
  4. temperaturein refluxing 1:1 THF/methanol
  5. additionadd excess cesium fluoride
  6. stirringStir for 10 minutes
  7. customremove solvent in vacuuo
  8. additionadd 10 mL of water
  9. extractionExtract with ethyl acetate

Sources & evidence

ORD record
ord-b97807f2f9624012a7e8a68ffe3f0489
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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