Ammonium Chloride → 6-(2,4-Difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one

HRID 2114555ノート

反応式

HRID 2114555 の反応式
C[O:2][C:3](=O)[CH:4]([O:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])[CH:5](O)[C:6]1[N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[CH:9][C:10]=1[N+:11]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[O:23][C:4]1[C:3](=[O:2])[NH:11][C:10]2[CH:9]=[N:8][N:7]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:6]=2[CH:5]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 598129592-(2,4-difluorophenoxy)-3-hydroxy-3-[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]propionic acid methyl ester

生成物 1

HCID 598129756-(2,4-Difluorophenoxy)-1-(2-trimethylsilanyl-ethoxymethyl)-1,4-dihydro-pyrazolo[4,3-b]pyridin-5-one収率 94.3%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒2 回HCID 962Water溶媒

実験手順

To a solution of 2-(2,4-difluorophenoxy)-3-hydroxy-3-[4-nitro-2-(2-trimethylsilanyl-ethoxymethyl)-2H-pyrazol-3-yl]propionic acid methyl ester (125 mg, 0.264 mmol) in ethanol (2 mL) and water (1 mL) was added ammonium chloride (74 mg, 5.2 eq) followed by iron powder (Fisher Brand, Electrolytic). The resulting mixture was stirred at room temperature for 45 minutes, refluxed overnight, cooled to room temperature, diluted with ethanol, and filtered through a 3 cm bed of celite with additional ethanol. The filtrate was concentrated, and the residue was diluted with ethyl acetate (80 mL) and water (40 mL). The organic layer was separated, washed with water (2×40 mL) and brine (1×40 mL), dried over magnesium sulfate, filtered and concentrated to give the title compound as a thick tan oil (98 mg, (M+H)+=394).

後処理

  1. temperaturerefluxed overnight
  2. temperaturecooled to room temperature
  3. filtrationfiltered through a 3 cm bed of celite with additional ethanol
  4. concentrationThe filtrate was concentrated
  5. additionthe residue was diluted with ethyl acetate (80 mL) and water (40 mL)
  6. customThe organic layer was separated
  7. washwashed with water (2×40 mL) and brine (1×40 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b006a1c7cec5442db9e5b23244302f5a
出典データセット
uspto-grants-2008_10
特許番号
US07435731B2

反応ノート

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