5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-3-nitro-pyridin-2-yl]-amide → 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-5-(2-chloro-phenyl)-1H-imidazo[4,5-b]pyridine

HRID 1191235Notes

Reaction equation

HRID 1191235 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([NH:14][C:15]([C:17]2[N:18]([CH3:27])[N:19]=[C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:21]=2[Cl:22])=O)[C:11]([N+:28]([O-])=O)=[CH:10][CH:9]=1>C(O)(=O)C.[Fe]>[C:23]([C:20]1[C:21]([Cl:22])=[C:17]([C:15]2[NH:28][C:11]3[C:12]([N:14]=2)=[N:13][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][CH:10]=3)[N:18]([CH3:27])[N:19]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 1

HCID 674124515-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-3-nitro-pyridin-2-yl]-amide

Product 1

HCID 1360731662-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-5-(2-chloro-phenyl)-1H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [6-(2-chloro-phenyl)-3-nitro-pyridin-2-yl]-amide (157 mg, 0.350 mmol, prepared as described in the previous step) in acetic acid (5 mL) was treated with iron powder (97.8 mg, 1.75 mmol) and heated to 100° C. for 3 h. The cooled mixture then was concentrated in vacuo, taken up in water (50 mL) and extracted twice with EtOAc (50 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 12-g SEPRA Si 50 SPE column (Isco system: Flow rate=15 mL/min; Eluent=EtOAc/hexanes, 1:99 v/v for 10 min, then 1:99 to 3:17 v/v over 40 min) to yield 2-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-5-(2-chloro-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. Mass Spectrum (LCMS, APCI pos.): Calculated for C20H19Cl2N5: 400.1 (M+H); Measured: 400.2.

Workup

  1. concentrationThe cooled mixture then was concentrated in vacuo
  2. extractionextracted twice with EtOAc (50 mL)
  3. dry with materialThe combined extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 12-g SEPRA Si 50 SPE column (Isco system

Sources & evidence

ORD record
ord-d139c36a31db41f78adc933ab7af605f
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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