Chloromethyl Methyl Ether → 3-(4-Fluoro-phenyl)-1-methoxymethyl-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine

HRID 659937Notes

Reaction equation

HRID 659937 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]=[C:17]([CH3:19])[CH:18]=[C:13]3[NH:12][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]=[C:17]([CH3:19])[CH:18]=[C:13]3[N:12]([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 251007503-(4-Fluoro-phenyl)-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 251008993-(4-Fluoro-phenyl)-1-methoxymethyl-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridineYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (22 mg, 0.55 mmole 60% in oil) is added to a solution of 150 mg (0.5 mmole) of 3-(4-Fluoro-phenyl)-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine (prepared as described in example 1) in 5 mL of dimethylformamide at room temperature. After 30 min. at room temperature, a solution of 44.5 mg of chloromethyl methyl ether in 0.5 mL of DMF is added to the reaction mixture. After 45 min. 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 after concentration is recrystallized into ethyl acetate/hexane mixture (1/2) to afford 70 mg of pure 3-(4-Fluoro-phenyl)-1-methoxymethyl-6-methyl-2-pyridin-4-yl-1H-pyrrolo[3,2-b]pyridine as a yellowish solid.

Workup

  1. waitAfter 45 min. at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solid residue after concentration
  6. customis recrystallized into ethyl acetate/hexane mixture (1/2)

Sources & evidence

ORD record
ord-ecf784c5bc6948cf9ff10710a119800b
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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