Water → HCID 10286124, compound

HRID 2243159Notes

Reaction equation

HRID 2243159 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2.[F:17][C:18]([F:30])([F:29])[O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.O>C(OCC)(=O)C>[F:17][C:18]([F:29])([F:30])[O:19][C:20]1[CH:25]=[CH:24][C:23]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 249055-BromoindoleHCID 27343864-(Trifluoromethoxy)phenylboronic acid

Product 1

HCID 10286124HCID 10286124, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A stirred slurry of 6.56 g (62 mmol) Na2CO3, 3.03 g (15.5 mmol) 5-bromoindole, 3.415 g (16.5 mmol) 4-(trifluoromethoxy)phenylboronic acid, and 0.50 g (0.43 mmol) tetrakistriphenylphosphine palladium was heated to reflux for 3 hr. The reaction mixture was allowed to cool and was then poured into 300 mL water and shaken with ethyl acetate. The combined aqueous and organic phases were filtered and the organic layer was separated, dried over MgSO4, and concentrated. The residue was chromatographed on silica (eluting with 20-33% EtOAc-hexane) to afford 2.49 g (58%) 5-[4-(trifluoromethoxy)phenyl]indole as a solid.

Workup

  1. temperatureto reflux for 3 hr
  2. temperatureto cool
  3. filtrationThe combined aqueous and organic phases were filtered
  4. customthe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica (eluting with 20-33% EtOAc-hexane)

Sources & evidence

ORD record
ord-b333a96a91684576a9685e80f4009d1a
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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