Hydrochloric Acid → HCID 10128517, compound

HRID 1297788Notes

Reaction equation

HRID 1297788 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.[F:43][C:44]([F:55])([F:54])[C:45]1[CH:50]=[CH:49][C:48](B(O)O)=[CH:47][CH:46]=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:48]3[CH:49]=[CH:50][C:45]([C:44]([F:55])([F:54])[F:43])=[CH:46][CH:47]=3)[C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10128517HCID 10128517, compoundYield 59%

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 (0.561 g, 0.932 mmol), 4-(trifluoromethyl)phenylboronic acid (0.354 g, 1.86 mmol), copper (II) acetate (0.169 g, 0.932 mmol), triethylamine (0.26 mL, 1.86 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 (0.498 g, 0.667 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (1.80 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 0.283 g (59%) of the title compound: mass spectrum (FAB): m/z=518(M+1); 1H NMR(DMSO-d6): δ8.32 (s, 2H), 7.98 (d, 2H), 7.79 (d, 2H), 7.40 (d, 1H), 7.32 (td, 1H), 7.21 (td, 1H), 6.99 (d, 1H), 6.80 (s, 4H), 2.13 (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-da1ace369dab4c5099e850d67ed9bb65
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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