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

HRID 1780552

반응식

HRID 1780552 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 86585711HCID 86585711, 화합물용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-c38e4cfaab654911b6722d8cb1c59be2
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05630962

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