Ethyl Acetate → HCID 67205348, compound

HRID 1615379Notes

Reaction equation

HRID 1615379 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:25]2[CH:30]=[C:29]([N+:31]([O-:33])=[O:32])[CH:28]=[CH:27][C:26]=2[CH3:34])O1.C(OCC)(=O)C>CN(C=O)C.O.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].O>[CH3:34][C:26]1[CH:25]=[CH:30][C:29]([N+:31]([O-:33])=[O:32])=[CH:28][C:27]=1[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6764936-BromoindoleHCID 177502694,4,5,5-Tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane

Product 1

HCID 67205348HCID 67205348, compoundYield 64.8%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

6-Bromo-1H-indole (203 mg, 1.04 mmol) and potassium carbonate (287 mg, 2.08 mmol) was dissolved in a DMF/water (4:1, 2.5 mL) mixture solution, and the gas included in the mixture solution was removed using ultrasonic wave and nitrogen gas. After sequentially adding 4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane (300 mg, 1.14 mmol) and Pd(dppf)Cl2 (85 mg, 0.10 mmol), the mixture was stirred at room temperature in a sealed reactor. 2 hours later, after adding ethyl acetate and water, the reaction solution was filtered through a diatomite pad. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried with anhydrous magnesium sulfate and then concentrated. Purification of the residue by chromatography (silica gel, EA:Hx=1:4) yielded 6-(2-methyl-5-nitrophenyl)-1H-indole (170 mg) as brown solid.

Workup

  1. customwas removed
  2. filtrationthe reaction solution was filtered through a diatomite pad
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customPurification of the residue by chromatography (silica gel, EA:Hx=1:4)

Sources & evidence

ORD record
ord-a1c7a106305947a0aa75a3a7c44c133b
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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