4-Nitrobenzoate → 5-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

HRID 489979Notes

Reaction equation

HRID 489979 reaction equation
[NH2:1][CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.[N+](C1C=CC([C:30]([O-])=[O:31])=CC=1)([O-])=O>ClCCl>[CH:30]([NH:1][CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[C:4]=1[C:15]1[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=1)=[O:31]

Participants

4

Reactant 2

HCID 44199404-NitrobenzoateHCID 220373405-Aminomethyl-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

Product 1

HCID 220373995-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-aminomethyl-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole (Example C-1) (8.04 g, 30 mmol) in 120 mL dichloromethane was added p-nitrophenylformate (6.01 g, 36 mmol) as a solid. The suspension was stirred for 24 h at room temperature and the solvents removed under reduced pressure. The residue was triturated with ether and filtered to obtain the desired 5-(N-formylaminomethyl)-4-(4-pyridyl)-3-(4-fluorophenyl)pyrazole derivative as a white solid: MS (M+H): 297 (base peak).

Workup

  1. customthe solvents removed under reduced pressure
  2. customThe residue was triturated with ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-71d7668c78a74dafb6cca1c27f2a0cf5
Source dataset
uspto-grants-2005_12
Patent number
US06979686B1

Reaction notes

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