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

HRID 849405ノート

反応式

HRID 849405 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a32d5c738da44ee385a620da10b56492
出典データセット
uspto-grants-2000_01
特許番号
US06011029

反応ノート

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