Cesium carbonate → 2-Cyclopropyl-4-methoxy-5-nitropyridine

HRID 715551

反応式

HRID 715551 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.O1CCOCC1>[CH:13]1([C:2]2[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 441196732-Chloro-4-methoxy-5-nitropyridine

生成物 1

HCID 867175992-Cyclopropyl-4-methoxy-5-nitropyridine収率 29.9%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 2-chloro-4-methoxy-5-nitropyridine (1.6 g, 8.48 mmol), cyclopropylboronic acid (1.458 g, 16.97 mmol), PdCl2(dppf)-CH2Cl2 adduct (1.386 g, 1.697 mmol), cesium carbonate (8.29 g, 25.5 mmol), and 1,4-Dioxane (15 mL) were heated using the microwave at 140° C. for 10 minutes. The reaction mixture was purified by normal phase chromatography (ISCO, 120 g silica, 0-3% methanol/DCM) to afford 2-cyclopropyl-4-methoxy-5-nitropyridine as a red solid (492 mg, 28%). MS (m/z) 195.0 (M+H+).

後処理

  1. temperaturewere heated
  2. customat 140° C.
  3. customfor 10 minutes
  4. customThe reaction mixture was purified by normal phase chromatography (ISCO, 120 g silica, 0-3% methanol/DCM)

出典と根拠

ORDレコード
ord-e36e9ffca7724bfbb6da5706df8dac70
出典データセット
uspto-grants-2015_11
特許番号
US09187464B2

関連ノート

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