4-(Trifluoromethyl)benzaldehyde → HCID 178506182, compound

HRID 1486564Notes

Reaction equation

HRID 1486564 reaction equation
[Br:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13]2[N:17]=[C:16]([NH2:18])[NH:15][N:14]=2)=[CH:4][C:3]=1[Cl:19].[F:20][C:21]([F:31])([F:30])[C:22]1[CH:29]=[CH:28][C:25]([CH:26]=O)=[CH:24][CH:23]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][C:5]([NH:12][C:13]2[N:17]=[C:16]([NH:18][CH2:26][C:25]3[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:30])[F:31])=[CH:29][CH:28]=3)[NH:15][N:14]=2)=[CH:4][C:3]=1[Cl:19]

Participants

5

Reactant 3

HCID 679964-(Trifluoromethyl)benzaldehydeHCID 4311764Sodium borohydrideHCID 72714613HCID 72714613, compound

Product 1

HCID 178506182HCID 178506182, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N3-(4-bromo-3-chloro-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 1 (50 mg, 140 μmol) and 4-(trifluoromethyl)benzaldehyde (48.8 mg, 280 μmol) in MeOH (3 ml) was stirred at room temperature for 2 days, NaBH4 (31.8 mg, 841 μmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was re-dissolved in DCM and was washed with water (2×4 ml), dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM) and recrystallized from DCM to give a light yellow powder as desired product (53 mg, 73% yield). MS +m/z: 514 (M+H)+

Workup

  1. customThe solvent was removed
  2. dissolutionthe reaction mixture was re-dissolved in DCM
  3. washwas washed with water (2×4 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 24 g, 3% to 5% MeOH in DCM)
  7. customrecrystallized from DCM

Sources & evidence

ORD record
ord-318568d4e0794ec6ab9c10880b726b8e
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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