Sodium Carbonate → 2-Methyl-3-nitro-6-phenylpyridine

HRID 849405노트

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HRID 849405 반응식
Cl.BrC1C=CC2N(CC3N=CNC=3)CC[N:9]([C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)=O)CC=2C=1.ClC1C([N+:39]([O-:41])=[O:40])=CC=C(C)N=1.[C:43]1(B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C(Cl)Cl>[C:25]1([C:24]2[CH:23]=[CH:22][C:21]([N+:39]([O-:41])=[O:40])=[C:19]([CH3:43])[N:9]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 12682302-Chloro-6-methyl-3-nitropyridineHCID 1784796677-Bromo-2,3,4,5-tetrahydro-1-(1H-imidazol-4-ylmethyl)-4-(1-naphthalenylcarbonyl)-1H-1,4-benzodiazepine, hydrochloride

생성물 1

HCID 149329632-Methyl-3-nitro-6-phenylpyridine

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

A mixture of Compound B and 2-chloro-3-nitro-6-methylpyridine (0.42 g, 2.40 mmol) in THF (10 mL) was degassed with nitrogen. Tetrakistriphenylphosphine palladium (28 mg, 0.024 mmol) was added and the mixture was stirred 30 minutes. 25 Phenylboronic acid (0.44 g, 3.6 mmol) and 2M Na2CO3 (1.8 mL) were added and the mixture was heated at 75° C. for 17 hours and stirred at room temperature for 48 hours. Methylene chloride was added and the mixture was filtered through celite and partitioned. The mixture was washed with saturated aqueous NaHCO3, dried (magnesium sulfate), filtered and evaporated to afford 0.77 g of brown solid. Flash chromatography (silica, 10% ethyl acetate/hexanes) afforded 0.37 g of Compound C (72%) as an off white solid and 0.05 g of 2-phenyl-3-nitro-6-methylpyridine (10%) as an oil.

후처리

  1. customwas degassed with nitrogen
  2. stirringstirred at room temperature for 48 hours
  3. filtrationthe mixture was filtered through celite
  4. custompartitioned
  5. washThe mixture was washed with saturated aqueous NaHCO3
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

출처 및 근거

ORD 기록
ord-a32d5c738da44ee385a620da10b56492
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011029

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