Hydrochloric Acid → HCID 10310991, compound

HRID 1297791Notes

Reaction equation

HRID 1297791 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.[CH3:43][O:44][C:45]1[CH:46]=[C:47](B(O)O)[CH:48]=[CH:49][CH:50]=1.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:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:25]=[C:26]([CH3:39])[C:27]([OH:31])=[C:28]([CH3:30])[CH:29]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:49]3[CH:48]=[CH:47][CH:46]=[C:45]([O:44][CH3:43])[CH:50]=3)[C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2734370(3-Methoxyphenyl)boronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10310991HCID 10310991, compoundYield 29%

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 (0.680 g, 1.13 mmol), 3-methoxyphenylboronic acid (0.343 g, 2.26 mmol), copper (II) acetate (0.205 g, 1.13 mmol), triethylamine (0.32 mL, 2.26 mmol), 4 angstrom molecular sieves, and dichloromethane (15 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite, and elute through a column of silica gel with 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.417 g, 0.589 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (1.47 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 0.155 g (29%) of the title compound: mass spectrum (FAB): m/z=480(M+1); 1H NMR(DMSO-d6): δ8.23 (s, 2H), 7.46 (t, 1H), 7.31 (d, 1H), 7.23 (td, 1H), 7.10 (td, 1H), 7.05-7.02 (m, 1H), 6.98-6.95 (m, 2H), 6.81 (d, 1H), 6.73 (s, 4H), 3.79 (s, 3H), 2.07 (s, 12H).

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-563f99ab4f644c98b4699c49d3d942da
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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