Dimethylformamide → 5-(3,4-Dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-1-one

HRID 2171016Notes

Reaction equation

HRID 2171016 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:14]OC)=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:17](=[O:20])([O-])[O-].[Cs+].[Cs+].BrC1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[NH:28][CH2:27]2.CN(C)[CH:36]=[O:37]>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>[CH3:10][O:9][C:8]1[C:3]([O:2][CH2:1][O:20][CH3:17])=[C:4]([C:14]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[C:29](=[O:33])[NH:28][CH2:27]3)[CH:5]=[CH:6][C:7]=1[O:37][CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 226071195-bromo-2,3-dihydro-1H-isoindol-1-oneHCID 67462911[3,4-Dimethoxy-2-(methoxymethyl)phenyl]boronic acid2×

Product 1

HCID 674677335-(3,4-Dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-1-one

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
90 °C

Procedure

To a stirring solution of 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid (compound 301) (400 mg, 1.88 mmol) in dimethylformamide (10 mL) under nitrogen atmosphere, were added cesium carbonate (1.8 g, 5.66 mmol), tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.09 mmol) and 5-bromoisoindolin-1-one (913 mg, 3.77 mmol) and the resultant reaction mixture was heated to 90° C. for 6 h. The reaction mixture was filtered off and the filtrate was extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine and dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification was done by column chromatography (silica gel, 0-3% methanol in dichloromethane) afforded 5-(3,4-dimethoxy-2-(methoxymethoxy)phenyl)isoindolin-1-one as a solid.

Workup

  1. customthe resultant reaction mixture
  2. filtrationThe reaction mixture was filtered off
  3. extractionthe filtrate was extracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-fd08901f6fbd4d72adee4f7890dd3fd1
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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