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

HRID 659946Notes

Reaction equation

HRID 659946 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-1d54c2d86eba4f2d9433949c5bfb0d6a
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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