Hydrochloric Acid → HCID 10310713, compound

HRID 1297789Notes

Reaction equation

HRID 1297789 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.[C:43]1([CH3:52])[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1B(O)O.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.O.ClCCl>[OH:31][C:27]1[C:26]([CH3:39])=[CH:25][C:24]([C:14]2([C:10]3[CH:11]=[C:12]([CH3:13])[C:7]([OH:6])=[C:8]([CH3:40])[CH:9]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=3[CH3:52])[C:15]2=[O:23])=[CH:29][C:28]=1[CH3:30]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27332672-Methylphenyl boronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10310713HCID 10310713, compoundYield 16%

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.700 g, 1.16 mmol), o-tolylboronic acid (0.316 g, 2.33 mmol), copper (II) acetate (0.211 g, 1.16 mmol), triethylamine (0.325 mL, 2.33 mmol), 4 angstrom molecular sieves, and dichloromethane (15 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite. Elute through a column of silica gel with 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.256 g, 3.70 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.92 mL). Stir for 1 h. Add 1N aqueous HCl(10 mL), water (40 mL), and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with ethyl acetate to give 0.086 g (16%) of the title compound: mass spectrum (FAB): m/z=464(M+1); 1H NMR(DMSO-d6): δ8.25 (s, 1H), 8.23 (s, 1H), 7.46-7.33 (m, 7H), 6.76 (s, 2H), 6.75 (s, 2H), 6.41 (d, 1H), 2.08 (s, 6H), 2.06 (s, 6H), 1.98 (s, 3H).

Workup

  1. filtrationFilter
  2. customthe reaction through Celite
  3. washElute through a column of silica gel with 70% dichloromethane in hexanes
  4. concentrationconcentrate
  5. stirringStir for 1 h
  6. customSeparate the layers
  7. concentrationconcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-5e5c974495e440d081909b8203e11e86
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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