4-Fluorobenzyl chloride → HCID 15096966, compound

HRID 345571Notes

Reaction equation

HRID 345571 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH3:10][NH:11][C:12]1[NH:20][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:14]=2[N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:17]2[CH:18]=[CH:19][C:14]3=[N:13][C:12]([NH:11][CH3:10])=[N:20][C:15]3=[CH:16]2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 10340Sodium CarbonateHCID 15096965HCID 15096965, compound

Product 1

HCID 15096966HCID 15096966, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5.6 parts of 1-(chloromethyl)-4-fluorobenzene, 5.2 parts of N-methyl-3H-imidazo[4,5-c]pyridine-2-amine, 4.2 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred and heated first for 3 hours at 90°-100° C. and further overnight at 60° C. The reaction mixture was poured onto water and the product was extracted four times with dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was boiled in 2-propanone, yielding 6 parts of 5-[(4-fluorophenyl)methyl]-N-methyl-5H-imidazo[4,5-c]pyridin-2-amine; mp. 209.5° C. (intermediate 97).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionthe product was extracted four times with dichloromethane
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (92.5:7.5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated

Sources & evidence

ORD record
ord-492b73f196ec4b86a1e983fce8b58044
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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