Triethylamine → HCID 10174790, compound

HRID 1297796Notes

Reaction equation

HRID 1297796 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.[Br:43][C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[CH:48][CH:49]=1.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[Br:43][C:44]1[CH:49]=[C:48]([N:16]2[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14]([C:10]3[CH:9]=[C:8]([CH3:40])[C:7]([OH:6])=[C:12]([CH3:13])[CH:11]=3)([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([OH:31])=[C:26]([CH3:39])[CH:25]=3)[C:15]2=[O:23])[CH:47]=[CH:46][CH:45]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2734318(3-Bromophenyl)boronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10174790HCID 10174790, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (2.0 g, 3.32 mmol), 3-bromophenylboronic acid (1.33 g, 6.64 mmol), copper (II) acetate (0.603 g, 3.32 mmol), triethylamine (0.93 mL, 6.64 mmol), 4 angstrom molecular sieves, and dichloromethane (50 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 to obtain 1.08 grams. Dissolve some of the resulting compound (0.167 g, 0.83 mmol) in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (2.1 mL). Stir for 1 h. Quench with 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 25% to 50% ethyl acetate in hexanes to give 0.255 g (62%) of the title compound: mass spectrum (ion spray): m/z=529(M+1), 531(M+3); 1H NMR(DMSO-d6): δ8.24 (s, 2H), 7.70-7.65 (m, 2H), 7.64-7.46 (m, 2H), 7.31 (d, 1H), 7.25 (td, 1H), 7.12 (t, 1H), 6.84 (d, 1H), 6.73 (s, 4H), 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. customto obtain 1.08 grams
  5. stirringStir for 1 h
  6. customQuench with saturated aqueous ammonium chloride(10 mL), water (40 mL) and ethyl acetate (50 mL)
  7. customSeparate the layers
  8. concentrationconcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-3b93e58b48b042bfb2afcec7e9e7537d
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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