Methanol → HCID 57743074、化合物

HRID 1926827ノート

反応式

HRID 1926827 の反応式
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][NH:8][C:9]2[C:10]([N+:24]([O-])=O)=[C:11]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.[CH3:29]O>[Ni]>[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:9]3=[N:19][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]3[N:24]=[CH:29]2)=[CH:5][CH:4]=1

参加物

4

反応物 2

HCID 887MethanolHCID 57742994HCID 57742994、化合物

生成物 1

HCID 57743074HCID 57743074、化合物収率 60%

試薬・触媒・溶媒 1

HCID 935Nickel触媒

反応条件

温度
150 °C

実験手順

Ethyl 2-[(4-methoxybenzyl)amino]-3-nitro-6-(trifluoromethyl)isonicotinate x193 (2.6 g, 6.5 mmol) is dissolved in methanol (100 ml), and Raney nickel (0.8 g) is added. The starting compound is hydrogenated in a Parr apparatus under a hydrogen pressure of 3 atm until the conversion of x193 is complete (1.5-2 h). The catalyst is filtered off and washed with methanol. The filtrate is evaporated to dryness. Triethyl orthoformate (100 ml) and p-toluene sulfonic acid (0.15 g) are added. The flask is equipped with a reflux condenser. The apparatus is flushed with argon, and the obtained reaction mixture is heated under vigorous stirring to 150° C. for 6 h. The reaction solution is evaporated in vacuum. The residue is partitioned between dichloromethane and a saturated aqueous solution of NaHCO3. The organic layer is dried with anhydrous sodium sulfate and evaporated. The target product is purified by chromatography on silicagel (dichloromethane/acetone) to afford 1.5 g of ethyl 3-(4-methoxybenzyl)-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine-7-carboxylate x196.

後処理

  1. custom(1.5-2 h)
  2. filtrationThe catalyst is filtered off
  3. washwashed with methanol
  4. customThe filtrate is evaporated to dryness
  5. additionTriethyl orthoformate (100 ml) and p-toluene sulfonic acid (0.15 g) are added
  6. customThe flask is equipped with a reflux condenser
  7. customThe apparatus is flushed with argon
  8. customthe obtained reaction mixture
  9. temperatureis heated
  10. customThe reaction solution is evaporated in vacuum
  11. customThe residue is partitioned between dichloromethane
  12. dry with materialThe organic layer is dried with anhydrous sodium sulfate
  13. customevaporated
  14. customThe target product is purified by chromatography on silicagel (dichloromethane/acetone)

出典と根拠

ORDレコード
ord-c4a7983a5408411b981e18fbd5a440b8
出典データセット
uspto-grants-2012_05
特許番号
US08183241B2

反応ノート

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