Sodium Iodide → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazole

HRID 1946348ノート

反応式

HRID 1946348 の反応式
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][N:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[C:19]([CH2:18][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)[CH:24]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 221055531-(Benzyloxy)-2-(bromomethyl)-4-chlorobenzeneHCID 178526745HCID 178526745、化合物

生成物 1

HCID 595479671-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazole収率 65.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Nitro-1H-pyrazole (Fluorochem) (0.505 g, 4.47 mmol) was dissolved in DMF (10 ml). Potassium carbonate (0.973 g, 7.04 mmol) and sodium iodide (75 mg, 0.50 mmol) were added. 2-(Bromomethyl)-4-chloro-1-[(phenylmethyl)oxy]benzene (WO2006066968) (1.33 g, 4.25 mmol) was added and washed in with further DMF (10 ml). The reaction was stirred at room temperature for 30 min, then concentrated in vacuo. The crude material was treated with water (150 ml). The aqueous mixture was extracted with EtOAc (3×150 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified on silica (70 g) using 0-100% EtOAc-cyclohexane. Appropriate fractions were concentrated in vacuo to give the title compound as a yellow solid (952 mg);

後処理

  1. washwashed in with further DMF (10 ml)
  2. concentrationconcentrated in vacuo
  3. additionThe crude material was treated with water (150 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×150 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica (70 g)
  8. concentrationAppropriate fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-62fb8a9bbc1e44a39e917f85edf5c169
出典データセット
uspto-grants-2013_03
特許番号
US08399436B2

反応ノート

読み込み中…