Diisopropyl Ether → 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-methoxypyridine

HRID 1670705ノート

反応式

HRID 1670705 の反応式
[Na].[CH3:2][C:3]1[N:4]([C:9]2[CH:14]=[CH:13][C:12](I)=[CH:11][N:10]=2)[C:5]([CH3:8])=[CH:6][CH:7]=1.[CH:16]([O:19]C(C)C)(C)C.[NH4+].[Cl-]>CO.[Cu]I.CN(C=O)C>[CH3:2][C:3]1[N:4]([C:9]2[CH:14]=[CH:13][C:12]([O:19][CH3:16])=[CH:11][N:10]=2)[C:5]([CH3:8])=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 7914Diisopropyl EtherHCID 25517Ammonium ChlorideHCID 14723912-(2,5-dimethyl-1H-pyrrol-1-yl)-5-iodopyridineHCID 5360545Sodium

生成物 1

HCID 7126392-(2,5-dimethyl-1H-pyrrol-1-yl)-5-methoxypyridine収率 100%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Sodium (3.0 equiv., 735 mmol, 16.9 g) was dissolved in dry methanol (240 ml). DMF (160 ml), CuI (0.15 equiv., 37 mmol, 7.0 g) and N-protected 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-iodo-pyridine (I17) (1.0 equiv., 245 mmol, 73.0 g) were added. The reaction mixture was heated to 80° C. for 3 h. After the mixture had been allowed to cool to room temperature, isopropylether and an aqueous NH4Cl solution (5%) were added, the mixture was stirred overnight. The solids were filtered off over Celite and the filtrate was extracted several times with dichloromethane. The combined organic phases were washed with a 10% aqueous NH4OH solution, dried with MgSO4 and concentrated in vacuo. After drying in high vacuum, 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-methoxy-pyridine (I18) (50 g, yield=100%) was pure enough to be used as such in the next step. 1H NMR (δ, CDCl3): 2.08 (6H, s), 3.91 (3H, s), 5.87 (2H, s), 7.15 (1H, d, J=8.7 Hz), 7.32 (1H, dd, J=8.7, 3.0 Hz), 8.27 (1H, d, J=3.0 Hz)

後処理

  1. temperatureto cool to room temperature
  2. filtrationThe solids were filtered off over Celite
  3. extractionthe filtrate was extracted several times with dichloromethane
  4. washThe combined organic phases were washed with a 10% aqueous NH4OH solution
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-03e4e0ac1de2456db6a43b8e27b5ec00
出典データセット
uspto-grants-2011_08
特許番号
US07994187B2

反応ノート

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