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

HRID 570276ノート

反応式

HRID 570276 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ab626a451f7a498f934a388a9c182619
出典データセット
uspto-grants-2015_05
特許番号
US09023846B2

反応ノート

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