Indole → HCID 9859162, compound

HRID 1296991Notes

Reaction equation

HRID 1296991 reaction equation
CC([O-])(C)C.[Na+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Br[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[F:23][C:20]1[CH:21]=[CH:22][C:17]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 798IndoleHCID 99931-Bromo-4-fluorobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 9859162HCID 9859162, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An oven dried resealable Schlenk tube was purged with argon and charged with Pd2(dba)3 (11.5 mg, 0.013 mmol, 5 mol % Pd), 2 [Example 1] (14.8 mg, 0.038 mmol, 7.5 mol %), NaOt-Bu (68 mg, 0.71 mmol) and indole (60 mg, 0.51 mmol). The tube was purged with argon then toluene (0.5 mL) and 1-bromo-4-fluorobenzene (55 μL, 0.50 mmol) were added through a rubber septum. The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at 100° C. for 36 h The reaction was then diluted with ether (20 mL), filtered through celite and concentrated in vacua. The crude material was purified by flash chromatography on silica gel to afford 81 mg (77%) of a colorless oil.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. customwas purged with argon
  3. customThe tube was purged with argon
  4. customThe septum was removed
  5. customthe tube was sealed with a teflon
  6. customscrew cap
  7. additionwas then diluted with ether (20 mL)
  8. filtrationfiltered through celite and
  9. concentrationconcentrated in vacua
  10. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-262d2dae19dd48cfbfbf024244f9ba10
Source dataset
uspto-grants-2007_07
Patent number
US07247731B2

Reaction notes

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