1,2-Dimethoxyethane → 4-(4-Nitrophenyl)pyridine

HRID 2236492

反応式

HRID 2236492 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>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.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 2734379(Pyridin-4-yl)boronic acid

生成物 1

HCID 2592194-(4-Nitrophenyl)pyridine収率 72%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

To a 25 mL round bottom flask is added 1-bromo-4-nitrobenzene (404 mg, 2.0 mmol), 4-pyridinylboronic acid (248 mg, 2.0 mmol), Na2CO3 (424 mg, 4.0 mmol) and Pd(PPh3)4 (100 mg, 0.087 mmol), DME (10 mL) and H2O (3 mL). The mixture is degassed and heated at reflux for 14 h. TLC is used to establish the completion of starting bromide, the mixture is allowed to cool to room temperature. EtOAc is added, and the EtOAc layer is washed with H2O (15 mL) and brine (10 mL) and dried over MgSO4. After removal of EtOAc, the resulting residue is subjected to flash chromatography with CH2Cl2/EtOAc (3:1) as eluent to provide the coupling product 4-(4-nitro-phenyl)-pyridine (288 mg, 72%). 1H NMR (400 MHz, CDCl3) ∂ 8.75 (2H, dd, J=6.0 and 2.8 Hz), 8.36 (2H, dd, J=9.6 and 3.2 Hz), 7.80 (2H, dd, J=8.8 and 2.4 Hz), 7.54 (2H, dd, J=5.6 and 2.0 Hz).

後処理

  1. customThe mixture is degassed
  2. temperatureheated
  3. temperatureat reflux for 14 h
  4. additionEtOAc is added
  5. washthe EtOAc layer is washed with H2O (15 mL) and brine (10 mL)
  6. dry with materialdried over MgSO4
  7. customAfter removal of EtOAc

出典と根拠

ORDレコード
ord-c31899243f804d249d8ce1dd54a9a4e5
出典データセット
uspto-grants-2010_05
特許番号
US07713994B2

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