Sodium Carbonate → HCID 58828884, compound

HRID 908323Notes

Reaction equation

HRID 908323 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]3)O1.Br[C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]=[CH:28][N:29]=[CH:30]2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CCO>[CH:30]1[C:31]2[C:26](=[C:25]([C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[C:15]([C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12]4)[CH:34]=[CH:33][CH:32]=2)[CH:27]=[CH:28][N:29]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 7364875-BromoisoquinolineHCID 58828895919363-25-0

Product 1

HCID 58828884HCID 58828884, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthoate (2.2 g, 7.0 mmol), 5-Bromoisoquinoline (1.33 g, 6.3 mmol), a 2M solution of sodium carbonate (9.6 mL) and palladium tetrakistriphenylphospine (0.37 g, 0.32 mmol) were heated in Toluene-EtOH (105 mL-21 mL) at 80° C. overnight. Solvent was evaporated and mixture was extracted with ethyl acetate. Organic phase was washed with brine, dried, filtered and evaporated. Residue was purified by chromatography (ethyl acetate-hexane 10:90->20:80->30:70->40:60->60-40. to give 1.4 g of the title compound as an off-white solid

Workup

  1. customSolvent was evaporated
  2. extractionmixture was extracted with ethyl acetate
  3. washOrganic phase was washed with brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customResidue was purified by chromatography (ethyl acetate-hexane 10:90->20:80->30:70->40:60->60-40

Sources & evidence

ORD record
ord-254d9feadf6c42949d969310108d3413
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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