4-Pyridinecarboxaldehyde → N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}pyridin-4-ylmethylamine

HRID 1634089Notes

Reaction equation

HRID 1634089 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][C:24]([CH:27]=O)=[CH:23][CH:22]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C.C(Cl)Cl>[F:18][C:17]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([C:13]([F:14])([F:15])[F:16])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:27][C:24]3[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=3)=[CH:7][CH:6]=2)[N:9]=1

Participants

7

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)anilineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18677115N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}pyridin-4-ylmethylamineYield 78%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.059 g, 0.2 mmol) and pyridine-4-carboxaldehyde (20 μL, 0.2 mmol) in methanol (0.8 mL) and acetic acid (0.2 mL) was stirred at room temperature for 15 minutes Sodium cyanoborohydride (0.032 g, 0.5 mmol) was added, and the reaction mixture stirred overnight. The reaction mixture was diluted with CH2Cl2 (50 mL), washed with brine (2×20 mL), dried over anhydrous Na2SO4 and evaporated. The residue was purified by flash column chromatography over silica gel (2% acetone in CH2Cl2) to give the above-named compound (0.060 g, 78%): mp 92-94° C. NMR (DMSO-d6) δ 4.40 (2H, d), 6.65 (2H, d), 6.97 (1H, t), 7.23 (2H, d), 7.35 (2H, d), 6.65 (2H, d), 7.7 (1H, s), 8.51 (2H, d).

Workup

  1. additionwas added
  2. washwashed with brine (2×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customThe residue was purified by flash column chromatography over silica gel (2% acetone in CH2Cl2)

Sources & evidence

ORD record
ord-b85b7fed82f349b5a86c037e7514868a
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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