Hydrochloric Acid → HCID 10288345, compound

HRID 1297792Notes

Reaction equation

HRID 1297792 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.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45](B(O)O)[CH:44]=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:8]([CH3:40])=[CH:9][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:45]3[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=3)[C:15]2=[O:23])=[CH:11][C:12]=1[CH3:13]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27343783-Pyridinylboronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10288345HCID 10288345, compoundYield 8%

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 (0.622 g, 1.03 mmol), pyridine-3-boronic acid (0.254 g, 2.07 mmol), copper (II) acetate (0.187 g, 1.03 mmol), triethylamine (0.29 mL, 2.07 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 50% dichloromethane in hexanes. Dissolve the resulting compound (0.103 g, 0.152 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0M) in THF (0.40 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 0.036 g (8%) of the title compound: mass spectrum (ion spray): m/z=451 (M+1); 1H NMR(DMSO-d6): δ8.70 (d, 1H), 8.65 (dd, 1H), 8.25 (s, 2H), 7.98-7.94 (m, 1H), 7.62-7.59 (m, 1H), 7.34 (d, 1H), 7.25 (td, 1H), 7.14 (td, 1H), 6.84 (d, 1H), 6.75 (s, 4H), 2.07 (s, 12H).

Workup

  1. filtrationFilter
  2. customthe reaction through Celite
  3. washElute through a column of silica gel with 50% dichloromethane in hexanes
  4. stirringStir for 1 h
  5. customSeparate the layers
  6. concentrationconcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-53278b8145314af38d5f1a8b4ed64171
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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