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

HRID 1107286

反応式

HRID 1107286 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl.Br[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1(P(CCCC[Pd-](Cl)Cl)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 201262(4-Methoxyphenyl)boronic acid

生成物 1

HCID 6038134-(4-Methoxyphenyl)pyridine

試薬・触媒・溶媒 2

HCID 178479790HCID 178479790、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

A mixture of 4-methoxybenzene boronic acid (2 g, 13.15 mmol), 4-bromopyridine hydrochloride (3.84 g, 19.72 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 1.5 hours under a nitrogen atmosphere. The solution was allowed to cool to ambient temperature, diluted with ethyl acetate (150 ml) and washed with water (150 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate and the solvents were removed leaving a white solid, which was chromatographed on silica gel in 70-100% ethyl acetate/hexane giving the title compound as a white solid (1.95 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.66-8.63 (2H, d, J=6.2 Hz), 7.63-7.59 (2H, d, J=9.0 Hz), 7.50-7.47 (2H, d, J=6.2 Hz), 7.03-6.99 (2H, d, J=9.0 Hz), and 3.87 (3H, s). m/z (ES+) 186 (M+1).

後処理

  1. temperatureto cool to ambient temperature
  2. washwashed with water (150 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customthe solvents were removed
  6. customleaving a white solid, which
  7. customwas chromatographed on silica gel in 70-100% ethyl acetate/hexane giving the title compound as a white solid (1.95 g, 80%)

出典と根拠

ORDレコード
ord-9a6730cc97d14ccdb48d0726af1da283
出典データセット
uspto-grants-2000_05
特許番号
US06060469

関連ノート

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