1,2-Dimethoxyethane → HCID 57930925, compound

HRID 1096947Notes

Reaction equation

HRID 1096947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11](OS(C(F)(F)F)(=O)=O)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[NH:21]1[C:29]2[C:24](=[CH:25][C:26](B(O)O)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COCCOC>C(OCC)(=O)C.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>[NH:21]1[C:29]2[C:24](=[CH:25][C:26]([C:11]3[CH:10]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[C:6]([O:8][CH3:9])=[O:7])=[CH:27][CH:28]=2)[CH:23]=[CH:22]1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 62657Potassium Phosphate, TribasicHCID 27343615-Indolylboronic acidHCID 54576351HCID 54576351, compound

Product 1

HCID 57930925HCID 57930925, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 3-methoxy-5-trifluoromethanesulfonyloxybenzoate (314 mg, 1.00 mmol), 5-indoleboronic acid (193 mg, 1.20 mmol), tetrakis(triphenylphosphine)palladium(0) (57.8 mg, 0.050 mmol), potassium phosphate (318 mg, 1.50 mmol) and 1,2-dimethoxyethane (5.0 ml) was stirred in a nitrogen atmosphere at 85° C. for 13 hours. After left cooled, the reaction mixture was diluted with ethyl acetate, filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography to obtain the title compound as a colorless oil.

Workup

  1. waitAfter left
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-3bb68a63e7384df9ab70ebb4fb4d500c
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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