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Hydrochloric Acid → 2-Fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid

HRID 1780557
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HRID 1780557 반응식
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1.[B:35](OC(C)C)([O:40]C(C)C)[O:36]C(C)C.Cl.[Cl-].[Na+]>O1CCCC1.CCCCCC>[F:13][C:14]1[C:19]([B:35]([OH:40])[OH:36])=[CH:18][CH:17]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:22][CH:21]=2)[N:15]=1
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참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 21531Triisopropyl borateHCID 179115002-(4-Octyloxyphenyl)-6-fluoropyridineHCID 178418339Butyllithium

생성물 1

HCID 19046950
2-Fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid
수율 78.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

8.00 ml (56.80 mmol) of diisopropylamine in 10 ml of tetrahydrofuran are stirred at 0° C. with 35.70 ml (56.80 mmol) of a 1.6-molar n-butyllithium solution in hexane for 1 hour. After cooling to -78° C., 8.56 g (28.40 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine (prepared as described in Example 2) in 1000 ml of tetrahydrofuran are added dropwise, and the mixture is stirred at -78° C. for 4 hours. 21.25 g (113.00 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 100 ml of 10% hydrochloric acid and stirring at room temperature for one 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 7.70 g of 2-fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid. ##STR29##

후처리

  1. stirringthe reaction mixture is stirred overnight, during which it
  2. customwarms to room temperature
  3. stirringstirring at room temperature for one 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-4962c978bc824e2e99e63ceab2130d15
출처 데이터셋
uspto-grants-1997_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05630962

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