Sodium Carbonate → HCID 16072742, compound

HRID 860749Notes

Reaction equation

HRID 860749 reaction equation
Br[C:2]1[N:3]([CH2:21][CH2:22][C:23]#[N:24])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:5]=2.[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)=O.[Li+].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]([C:22]1[CH2:21][N:3]2[C:4]3[CH:5]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[CH:7]=[CH:8][C:9]=3[C:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=[C:2]2[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:25]=1)#[N:24]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2921892-Formylphenylboronic acidHCID 433294Lithium ChlorideHCID 58765170HCID 58765170, compound

Product 1

HCID 16072742HCID 16072742, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine)palladium(0) (207 mg, 0.18 mmol) was added to a stirred and degassed mixture of methyl 2-bromo-1-(2-cyanoethyl)-3-cyclohexyl-1H-indole-6-carboxylate (695 mg, 1.8 mmol), 2-formylphenyl boronic acid (233 mg, 1.56 mmol), LiCl (151 mg, 3.57 mmol) in ethanol (5.8 mL) and toluene (5.8 mL) containing 1M aqueous sodium carbonate (5 mL, 5 mmol). The mixture was stirred under reflux for 2 hr. The mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water (2×), followed by brine, and dried over sodium sulfate. The extract was concentrated and partially purified by chromatography on SiO2 (35 g) using the flash technique and eluting with methylene chloride with between 10–20% ethyl acetate. A solution of the residue when stood in methanol deposited yellow needles of the titled compound. MS m/z 397 (MH+); (500 MHz, CHLOROFORM-D) δ ppm 1.31–2.16 (m, 10 H) 2.73–2.89 (m, 1 H) 3.97 (s, 3 H) 4.46 (s, 1 H) 5.00–5.17 (m, 1 H) 7.41–7.47 (m, 1 H) 7.49–7.53 (m, 1 H) 7.55 (s, 1 H) 7.57–7.61 (m, 1 H) 7.79 (d, J=8.55 Hz, 1 H) 7.91 (d, J=8.55 Hz, 1 H) 8.18 (s, 1 H).

Workup

  1. customdegassed
  2. stirringThe mixture was stirred
  3. temperatureunder reflux for 2 hr
  4. temperatureThe mixture was cooled
  5. washThe organic layer was washed with water (2×)
  6. dry with materialdried over sodium sulfate
  7. concentrationThe extract was concentrated
  8. custompartially purified by chromatography on SiO2 (35 g)
  9. washeluting with methylene chloride with between 10–20% ethyl acetate

Sources & evidence

ORD record
ord-ee4298f1cba74a42898052bcfc784eda
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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