Triethylamine → HCID 10196037, compound

HRID 1297797Notes

Reaction equation

HRID 1297797 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][C:50]=1[O:51][CH3:52].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.ClCCl>[CH3:43][O:44][C:45]1[CH:46]=[C:47]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:24]3[CH:25]=[C:26]([CH3:39])[C:27]([OH:31])=[C:28]([CH3:30])[CH:29]=3)([C:10]3[CH:11]=[C:12]([CH3:13])[C:7]([OH:6])=[C:8]([CH3:40])[CH:9]=3)[C:15]2=[O:23])[CH:48]=[CH:49][C:50]=1[O:51][CH3:52]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10196037HCID 10196037, compoundYield 31%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 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 (0.583 g, 0.968 mmol), 3,4-dimethoxybenzeneboronic acid (0.353 g, 1.94 mmol), copper (II) acetate (0.176 g, 0.968 mmol), triethylamine (0.27 mL, 1.94 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 (0.399 g, 0.511 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0M) in THF (1.35 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(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 a gradient from 25% to 50% ethyl acetate in hexanes to give 0.153 g (31%) of the title compound: mass spectrum (ion spray): m/z=510(M+1); 1H NMR(DMSO-d6): δ8.23 (s, 2H), 7.31 (d, 1H), 7.21 (td, 1H), 7.11-7.06 (m, 2H), 6.94-6.89 (m, 2H), 6.76-6.74 (m, 5H), 3.80 (s, 3H), 3.75 (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-19b551e2a26b485897d2f88a483f6ad0
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

Loading…