Chloromethyl Methyl Ether → 3-(4-Fluoro-phenyl)-1-methoxymethoxy-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine

HRID 659946ノート

反応式

HRID 659946 の反応式
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]([OH:19])[C:11]=2[C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:6][CH:5]=1.[CH3:26][O:27][CH2:28]Cl.[Cl-].[NH4+]>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[N:12]([O:19][CH2:26][O:27][CH3:28])[C:11]=2[C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 52882383-(4-Fluorophenyl)-1-Hydroxy-2-(Pyridin-4-Yl)-1h-Pyrrolo(3,2-B)Pyridine

生成物 1

HCID 251012123-(4-Fluoro-phenyl)-1-methoxymethoxy-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine収率 52.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (30 mg, 0.72 mmole 60% in oil) is added to a solution of 200 mg (0.65 mmole) of 3-(4-Fluoro-phenyl)-2-pyridin-4-yl-pyrrolo[3,2-b]pyridin-1-ol in 6 mL of dimethylformamide at room temperature. After 30 min. at room temperature, 65 mg of chloromethyl methyl ether is added to the reaction mixture. After 1 hour at room temperature, the reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue is purified by chromatography on silica gel (ethylacetate) to give 120 mg of 3-(4-Fluoro-phenyl)-1-methoxymethoxy-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine as white crystals.

後処理

  1. waitAfter 1 hour at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solid residue is purified by chromatography on silica gel (ethylacetate)

出典と根拠

ORDレコード
ord-1d54c2d86eba4f2d9433949c5bfb0d6a
出典データセット
uspto-grants-2011_12
特許番号
US08084395B2

反応ノート

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