Hydrochloric Acid → HCID 66841346, compound

HRID 1929206Notes

Reaction equation

HRID 1929206 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]2.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>C(O)CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([C:11]([OH:13])=[O:12])[NH:6]3)=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 40426044-bromo-1H-indole-2-carboxylic acid

Product 1

HCID 66841346HCID 66841346, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

4-Bromo-1H-indole-2-carboxylic acid (5 g, 20.8 mmol) and 4-methoxy-phenyl-boronic acid (3.2 g, 20.8 mmol) are dissolved in 1-propanol (100 ml) and the mixture is flushed with argon for 30 min. Then bis(triphenylphosphin)palladium(II)chloride (200 mg, 1 mmol) and Na2CO3 (4.4 g, 40.2 mmol) are added and the reaction mixture is stirred at 85° C. for 3 h. After cooling down to room temperature, ethyl acetate and 2M HCl are added. The organic layers are dried over sodium sulphate. Evaporation gave 6 g of an beige solide, which is further purified by crystallisation from ethyl acetate.

Workup

  1. customthe mixture is flushed with argon for 30 min
  2. temperatureAfter cooling down to room temperature
  3. dry with materialThe organic layers are dried over sodium sulphate
  4. customEvaporation
  5. customgave 6 g of an beige solide, which
  6. customis further purified by crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-af68e3efb4794f428a1bb9d56d2df8e0
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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