Formaldehyde → (8-(3-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-yl)methanol

HRID 546663Notes

Reaction equation

HRID 546663 reaction equation
C=O.[H-].[Na+].[F:5][C:6]1[CH:7]=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]3[N:18]=[C:19](/[CH:21]=[CH:22]/[C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]5)=[C:25]([O:35][CH3:36])[CH:24]=4)[N:20]=[C:13]23)[CH:9]=[CH:10][CH:11]=1.O.[C:38](=O)(O)[O-:39].[Na+]>CN(C=O)C.C(OCC)(=O)C>[F:5][C:6]1[CH:7]=[C:8]([C:12]2([CH2:38][OH:39])[CH2:17][CH2:16][CH2:15][N:14]3[N:18]=[C:19](/[CH:21]=[CH:22]/[C:23]4[CH:28]=[CH:27][C:26]([N:29]5[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30]5)=[C:25]([O:35][CH3:36])[CH:24]=4)[N:20]=[C:13]23)[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 24758Sodium hydrideHCID 25212802HCID 25212802, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66839396(8-(3-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridin-8-yl)methanol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Paraformaldehyde (186 mg) and sodium hydride (containing 40% of mineral oil, 28.7 mg) were added to a solution of 8-(3-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine synthesized by the method in Examples 1 and 2 (154 mg) in DMF (3 mL), and the reaction solution was stirred at room temperature for 30 minutes. Thereafter, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 204 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e354777320b4186bb0a274837d7adda
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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