Sodium Carbonate → HCID 21198039, compound

HRID 1066074Notes

Reaction equation

HRID 1066074 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](B(O)O)=[CH:3][N:2]=1.C(O[N:19]1[CH2:24][CH2:23][C:22](OS(C(F)(F)F)(=O)=O)=[CH:21][C:20]1=C=O)(C)(C)C.[Cl-].[Li+].[C:37](=[O:40])([O-])[O-:38].[Na+].[Na+]>O1CCCC1.CO>[C:5]([O:38][C:37]([N:19]1[CH2:24][CH2:23][C:22]([C:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=[N:2][CH:3]=2)=[CH:21][CH2:20]1)=[O:40])([CH3:10])([CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 3761204Isoquinoline-4-boronic acidHCID 86756984HCID 86756984, compound

Product 1

HCID 21198039HCID 21198039, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.5 gm (14.5 mMol) isoquinolin-4-ylboronic acid, 3.43 gm (10.3 mMol) 1-tert-butoxy-carbonyl-4-trifluoromethanesulfonyloxy-1,2,5,6-tetrahydropyridine, 1.3 gm (30.9 mMol) lithium chloride, 0.04 gm (0.05 mMol) [1,1′-bis (diphenylphosphino)-1-ferrocene]-palladium II chloride, and 2 mL 2M aqueous sodium carbonate in about 20 mL tetrahydrofuran containing a few drops of methanol was stirred at reflux for about 4 hours. The reaction was cooled to room temperature and then partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 3:2 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.216 gm (57%) 1-tert-butoxycarbonyl-4-(isoquinolin-4-yl)-1,2,5,6-tetrahydropyridine as a light yellow oil.

Workup

  1. temperatureat reflux for about 4 hours
  2. custompartitioned between ethyl acetate and 2N sodium hydroxide
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted well with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 3:2 hexane
  9. additionFractions containing product
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-edf2201e243845818b5bf75b8f8288fd
Source dataset
uspto-grants-2001_06
Patent number
US06242450B1

Reaction notes

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