Potassium Phosphate, Tribasic → 1-Benzyl-3-(hydroxymethyl)-5-mesitylcinnolin-4(1H)-one

HRID 598164Notes

Reaction equation

HRID 598164 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13](Cl)[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20][OH:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([CH3:33])[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[C:23]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=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>[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:23]3[C:24]([CH3:29])=[CH:25][C:26]([CH3:28])=[CH:27][C:22]=3[CH3:33])[CH:14]=[CH:15][CH:16]=2)[C:11](=[O:19])[C:10]([CH2:20][OH:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2921842,4,6-Trimethylbenzeneboronic acidHCID 672672091-Benzyl-5-chloro-3-hydroxymethylcinnolin-4(1H)-one

Product 1

HCID 672677011-Benzyl-3-(hydroxymethyl)-5-mesitylcinnolin-4(1H)-oneYield 47.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.144 g (0.479 mmol) of 1-benzyl-5-chloro-3-(hydroxymethyl)cinnolin-4(1H)-one, 0.126 g (0.766 mmol) of mesityl boronic acid, 0.111 g (0.096 mmol) of tetrakis and 0.254 g (1.20 mmol) of potassium phosphate in 8 mL of DMF was heated to 100° C. for 16 h. The reaction mixture was quenched with water and extracted with ethyl acetate containing 5% hexanes. The combined organic layers were washed with brine, dried over sodium sulfate, filtered through a plug of silica gel and concentrated in vacuo onto silica gel. The crude material was purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 0.087 g (47%) of the title compound as a tan solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate containing 5% hexanes
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered through a plug of silica gel
  6. concentrationconcentrated in vacuo onto silica gel
  7. customThe crude material was purified by flash chromatography
  8. washeluting with a 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-4cc07d99854542ee8e7e02513e48ee6d
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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