Triethylamine → HCID 10239083, compound

HRID 1297794Notes

Reaction equation

HRID 1297794 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.[CH2:43]([O:45][C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1)[CH3:44].C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[CH2:43]([O:45][C:46]1[CH:51]=[C:50]([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:49]=[CH:48][CH:47]=1)[CH3:44]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27739203-Ethoxybenzeneboronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10239083HCID 10239083, compoundYield 62.2%

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 (0.500 g, 0.831 mmol), 3-ethoxyphenylboronic acid (0.276 g, 1.66 mmol), copper (II) acetate (0.151 g, 0.831 mmol), triethylamine (0.23 mL, 1.66 mmol), 4 angstrom molecular sieves, and dichloromethane (20 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 (0.603 g, 0.83 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0M) 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=494(M+1); 1H NMR(DMSO-d6); δ8.28 (s, 2H), 7.51 (t, 1H), 7.37 (d, 1H), 7.29 (td, 1H), 7.16 (td, 1h), 7.08-7.06 (m, 1H), 7.02-6.98 (m, 2H), 6.87 (d, 1H), 6.80 (s, 4H), 4.12 (q, 2H), 2.12(s, 12H), 1.38 (t, 3H).

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. 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-1d07756d7859440db15ccdbc76b0ce3c
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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