Potassium Carbonate → HCID 20100022, compound

HRID 402308Notes

Reaction equation

HRID 402308 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7](CCCCCCCC)[CH:6]=[C:5]2CN(C)C.F[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)N(CCCCCCCC)C=[C:27]2CN1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:26]1([CH3:27])[CH:30]=[CH:31][CH:32]=[C:24]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH:25]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 50915660HCID 50915660, compoundHCID 50916158HCID 50916158, compound

Product 1

HCID 20100022HCID 20100022, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 5-bromo-1H-indole (1, 5 mmol, 1 equiv.), 3-tolylboronic acid (2, 5.5 mmol, 1.1 equiv.) and Pd(dppf)Cl2 (0.25 mmol, 0.05 equiv.) in 12 mL 1,4-dioxane was added 4 mL aqueous solution of K2CO3 (15 mmol, 3 equiv.). The mixture was stirred under argon for about 15 min then stirred under microwave in 130□ for about 25 min twice. On cooling, the solvent was evaporated and the resulting residue was extracted with CH2Cl2 (20 mL×3), the dichloromethane layer was washed with brine, dried (Na2SO4) and filtered. The residue obtained on removal of the solvent was purified by column chromatography on silica gel with EtOAc/hexane as eluting solvents to give the target compound 5-m-tolyl-1H-indole (3). Yield: 55.0%. 1H NMR (300 MHz, CDCl3): δ 2.31 (s, 3 H), 6.47 (s, 1 H), 6.92-7.12 (m, 2 H), 7.18-7.23 (m, 1 H), 7.29-7.35 (m, 4H), 7.74 (s, 1 H), 7.99 (br, 1H). 13C NMR (75 MHz, CDCl3) δ 21.5, 102.9, 111.1, 119.2, 121.9, 124.4, 124.8, 127.0, 128.2, 128.3, 128.5, 133.4, 135.2, 138.1, 142.5.

Workup

  1. stirringthen stirred under microwave in 130□ for about 25 min twice
  2. temperatureOn cooling
  3. customthe solvent was evaporated
  4. extractionthe resulting residue was extracted with CH2Cl2 (20 mL×3)
  5. washthe dichloromethane layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe residue obtained on removal of the solvent
  9. customwas purified by column chromatography on silica gel with EtOAc/hexane
  10. washas eluting solvents

Sources & evidence

ORD record
ord-1da6d07fd4a84a8a8dc900b8009a11e5
Source dataset
uspto-grants-2014_06
Patent number
US08742100B2

Reaction notes

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