Hydrochloric Acid → 2-Fluoro-6-octyloxypyridine-3-boronic acid

HRID 1780552

Reaction equation

HRID 1780552 reaction equation
C([N-]C(C)C)(C)C.[Li+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:11]=1.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.Cl.[Cl-].[Na+]>O1CCCC1.CCCCCC.C(C1C=CC=CC=1)C.O1CCCC1>[F:9][C:10]1[C:15]([B:25]([OH:30])[OH:26])=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:11]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 190469372-Fluoro-6-octyloxypyridine

Product 1

HCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acidYield 58.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 86585711HCID 86585711, compoundSolvent

Procedure

34.62 ml (69.24 mmol) of a 2-molar solution of lithium diisopropylamide in tetrahydrofuran/hexane/ethylbenzene are added dropwise at -78° C. to 13.00 g (57.70 mmol) of 2-fluoro-6-octyloxypyridine in 200 ml of tetrahydrofuran, and the mixture is stirred for 4 hours. 26.05 g (138.48 mmol) of triisopropyl borate are then added dropwise at -78° C., and the reaction mixture is stirred overnight, during which it warms to room temperature. After addition of 80 ml of 10% hydrochloric acid and stirring at room temperature for 1 hour, sodium chloride solution is added, the mixture is extracted with ether, the ether phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Recrystallization from acetonitrile gives 9.03 g (33.55 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid. ##STR22##

Workup

  1. stirringthe reaction mixture is stirred overnight, during which it
  2. customwarms to room temperature
  3. stirringstirring at room temperature for 1 hour
  4. extractionthe mixture is extracted with ether
  5. washthe ether phase is washed with sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-c38e4cfaab654911b6722d8cb1c59be2
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Linked notes

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