Ethyl Acetate → 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine

HRID 570276Notes

Reaction equation

HRID 570276 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=2)=O)[C:5]([N+:21]([O-])=O)=[CH:4][N:3]=1.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[N:3]=[CH:4][C:5]2[NH:21][C:9]([C:11]3[N:12]([CH3:20])[N:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=3)=[N:8][C:6]=2[CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 866574325-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide

Product 1

HCID 1363374486-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid (2-bromo-5-nitro-pyridin-4-yl)-amide (79.8 mg, 0.183 mmol, prepared as described in the previous step) in acetic acid (1 mL) was treated with Fe powder (102 mg, 1.82 mmol). The resulting mixture was stirred at 110° C. for 1 h, cooled to room temperature, and treated with EtOAc (10 mL) and saturated NaHCO3 (10 mL). The organic layer was separated, washed with saturated NaHCO3 (10 mL), H2O (10 mL), concentrated, and the resulting residue dried in vacuo to yield 6-bromo-2-(5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-3H-imidazo[4,5-c]pyridine. 1H-NMR (400 MHz, CDCl3) δ: 10.0 (br s, 1H), 8.80 (br s, 1H), 7.60 (br s, 1H), 6.60 (m, 1H), 4.40 (s, 3H), 1.30 (s, 9H).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3 (10 mL), H2O (10 mL)
  4. concentrationconcentrated
  5. customthe resulting residue dried in vacuo

Sources & evidence

ORD record
ord-ab626a451f7a498f934a388a9c182619
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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