Sodium Carbonate → 5-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

HRID 1918859ノート

反応式

HRID 1918859 の反応式
[CH3:1][N:2]1[CH2:7][CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH2:4][CH2:3]1.Br[C:18]1[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[N:22][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH:6]=[C:5]([C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[N:22][CH:23]=2)[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 8176205-Bromo-2-nitropyridineHCID 207733711-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

生成物 1

HCID 580442465-(1-Methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

To a round-bottomed flask equipped with a stirring bar, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (1.50 g, 6.72 mmol), 5-bromo-2-nitropyridine (1.64 g, 8.07 mmol), Pd(PPh3)4 (388 mg, 0.336 mmol), Na2CO3 aqueous solution (1.0 N, 20.2 mL, 20.2 mmol), dioxane (60.6 mL) were added. The reaction mixture was heated at 100° C. for 10 hrs. CH2Cl2 (200 mL) was added to the resulting mixture was washed with water (30 mL×3). CH2Cl2(200 mL) was added and the resulting mixture was washed with water (30 mL×3), brine (30 mL×1), dried over MgSO4, filtered, and removed solvent in vacuo. Silica gel column chromatography (MeOH:DCM=5:95) gave 5-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-2-nitropyridine (130a) as a yellow solid.

後処理

  1. customTo a round-bottomed flask equipped with a stirring bar
  2. washwas washed with water (30 mL×3)
  3. additionCH2Cl2(200 mL) was added
  4. washthe resulting mixture was washed with water (30 mL×3), brine (30 mL×1)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customremoved solvent in vacuo

出典と根拠

ORDレコード
ord-bae2bc32ee6a4bc0b1057e521d601007
出典データセット
uspto-grants-2013_12
特許番号
US08618107B2

反応ノート

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