Triethylamine → HCID 10310500, compound

HRID 1297793Notes

Reaction equation

HRID 1297793 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][C:46](B(O)O)=[CH:45][CH:44]=1.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>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:46]3[CH:47]=[CH:48][N:43]=[CH:44][CH:45]=3)[C:15]2=[O:23])=[CH:29][C:28]=1[CH3:30]

Participants

11

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 2734379(Pyridin-4-yl)boronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10310500HCID 10310500, compoundYield 21%

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), pyridine-4-boronic acid (0.286 g, 2.33 mmol), copper (II) acetate (0.211 g, 1.16 mmol), triethylamine (0.33 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 10% ethyl acetate in hexanes. Dissolve the resulting compound (0.103 g, 0.152 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.40 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(10 mL), water (40 mL)m and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with a gradient from 50% to 75% ethyl acetate in hexanes to give 0.109 g (21%) of the title compound: mass spectrum (ion spray): m/z=451(M+1); 1H NMR(DMSO-d6): δ8.46 (dd, 2H), 8.27 (s, 2H), 7.59 (dd, 2H), 7.34 (d, 1H), 7.29 (t, 1H), 7.16 (t, 1H), 7.06(d, 1H), 6.73 (s, 4H), 2.06(s, 12H).

Workup

  1. filtrationFilter
  2. customthe reaction through Celite
  3. washElute through a column of silica gel with 10% ethyl acetate in hexanes
  4. stirringStir for 1 h
  5. customSeparate the layers
  6. concentrationconcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-ed42a77700894b8abfce356df1be3a8e
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

Loading…