Diisopropylamine → 4-Fluoro-3-methyl-5-(tributylstannyl)pyridine

HRID 2069094노트

반응식

HRID 2069094 반응식
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20].[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24].C(=O)(O)[O-].[Na+]>C1COCC1>[F:13][C:14]1[C:19]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])=[CH:18][N:17]=[CH:16][C:15]=1[CH3:20]

참가 물질

7

반응물 5

HCID 7912DiisopropylamineHCID 15096Tributyltin ChlorideHCID 516892Sodium BicarbonateHCID 27629214-Fluoro-3-methylpyridineHCID 178418339Butyllithium

생성물 1

HCID 595351114-Fluoro-3-methyl-5-(tributylstannyl)pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A THF (1 mL) solution of diisopropylamine (160 μL; WAKO) was cooled to −78° C. under a nitrogen atmosphere followed by the dropwise addition of normal butyllithium (2.6 M, 430 μL; KANTO). The resulting mixture was stirred as it was for 30 minutes followed by the dropwise addition of a THF (1 mL) solution of 4-fluoro-3-methylpyridine (111 mg) and the resulting mixture was further stirred for 1 hour. Then tri-n-butyltin chloride (330 μL; TCI) was added and the resulting mixture was slowly raised to room temperature and then stirred for 2 hours. Saturated aqueous sodium bicarbonate solution was added to the reaction mixture solution, to the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine. The organic layer was dried and the solvent was evaporated under reduced pressure to give the title compound.

후처리

  1. stirringthe resulting mixture was further stirred for 1 hour
  2. stirringstirred for 2 hours
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. customThe organic layer was dried
  6. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-ec39fc47cccd4e13b10468c81d75859a
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299055B2

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