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

HRID 659946노트

반응식

HRID 659946 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1d54c2d86eba4f2d9433949c5bfb0d6a
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084395B2

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