Potassium Carbonate → HCID 66713022, compound

HRID 1406124Notes

Reaction equation

HRID 1406124 reaction equation
CB1OB(C)OB(C)O1.[C:10]([O-])([O-])=O.[K+].[K+].C(OC(C1N=C(Cl)C2C(C=1O)=CC(OC1C=CC=CC=1)=CC=2)=O)CCC.[CH2:42]([O:46][C:47]([C:49]1[N:50]=[C:51](Cl)[C:52]2[C:57]([C:58]=1[OH:59])=[CH:56][CH:55]=[C:54]([O:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH:53]=2)=[O:48])[CH2:43][CH2:44][CH3:45]>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.O1CCOCC1>[CH2:42]([O:46][C:47]([C:49]1[N:50]=[C:51]([CH3:10])[C:52]2[C:57]([C:58]=1[OH:59])=[CH:56][CH:55]=[C:54]([O:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[CH:53]=2)=[O:48])[CH2:43][CH2:44][CH3:45]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 86595469HCID 86595469, compoundHCID 86595470HCID 86595470, compound

Product 1

HCID 66713022HCID 66713022, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of anhydrous 1,4-dioxane (200 ml), Pd(PPh3)4 (3.47 g, 3 mmol), trimethylboroxine (4.22 ml, 30 mmol), and K2CO3 (12.44 g, 90 mmol) was added a regioisomeric mixture of 1-chloro-4-hydroxy-6-phenoxy-isoquinoline-3-carboxylic acid butyl ester and 1-Chloro-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid butyl ester (11.15 g, 30 mmol). The mixture was refluxed under N2-protection with stirring for 3 h and was then stirred at ambient temperature for 48 h. Subsequently, the mixture was concentrated in vacuo. To the residue was added water (100 ml) and the mixture was extracted with EtOAc (300 ml). The organic phase was dried over MgSO4 and evaporated in vacuo. Purification of the residue by flash column chromatography on silica gel using hexanes:EtOAc=9:1 as the eluent gave the title compound as a yellowish solid (4.40 g, first fraction); MS-(+)-ion M+1=352.1.

Workup

  1. additionwas added
  2. temperatureThe mixture was refluxed under N2-protection
  3. stirringwas then stirred at ambient temperature for 48 h
  4. concentrationSubsequently, the mixture was concentrated in vacuo
  5. additionTo the residue was added water (100 ml)
  6. extractionthe mixture was extracted with EtOAc (300 ml)
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated in vacuo
  9. customPurification of the residue by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-751d8f1cb8d84d16936d1839ed70c484
Source dataset
uspto-grants-2014_12
Patent number
US08916585B2

Reaction notes

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