Sodium Carbonate → HCID 22032967, compound

HRID 2221276Notes

Reaction equation

HRID 2221276 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.[Cl:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1.CCO.O>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.O>[Cl:17][C:18]1[CH:23]=[C:22]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]=[CH:11]3)[CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 249055-BromoindoleHCID 2734323(3-Chlorophenyl)boronic acidHCID 19096565Water ethanol

Product 1

HCID 22032967HCID 22032967, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A stirred slurry of 4.23 g (40 mmol) Na2CO3, 1.84 g (9.4 mmol) 5-bromoindole, 1.88 g (10 mmol) 3-chlorophenylboronic acid, and 0.29 g (0.25 mmol) Pd(PPh3)4 in 50 mL 1:1 EtOH-water was heated to reflux for 2.5 hours. The reaction mixture was allowed to cool and was then poured into 400 mL water and extracted with EtOAc. The organic layer was separated, dried over MgSO4, and concentrated to afford 2.15 g crude 5-(3-chlorophenyl)indole as a tan solid.

Workup

  1. temperatureto reflux for 2.5 hours
  2. temperatureto cool
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-705a8ba3253b4d4b82b2e2abb4f7ea05
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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