Sodium hydride → Ethyl 8-[(4-chlorophenoxy)methyl]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

HRID 71177

反応式

HRID 71177 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][CH:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.[H-].[Na+].[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39]Cl)=[CH:34][CH:33]=1.[Cl-].[NH4+]>CN(C=O)C>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:23]2([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:21][CH2:20][N:19]3[C:15]([C:5]4[CH:6]=[CH:7][C:8]([C:9]5[O:13][C:12]([CH3:14])=[N:11][CH:10]=5)=[C:3]([O:2][CH3:1])[CH:4]=4)=[N:16][N:17]=[C:18]23)=[CH:34][CH:33]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 88801alpha,4-DichloroanisoleHCID 66608236Ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate

生成物 1

HCID 66608313Ethyl 8-[(4-chlorophenoxy)methyl]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate収率 32.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Under ice-cooling and an argon stream, to a mixture of ethyl 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (1000 mg) in DMF (15 mL) was added sodium hydride (60%, 115 mg), and the mixture was stirred at 0° C. for 30 min. 1-Chloro-4-(chloromethoxy)benzene (694 mg) was added, and the mixture was stirred at 0° C. for 1 hr. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (440 mg).

後処理

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was stirred at 0° C. for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-bc044d32620040e5ba889697abd459b4
出典データセット
uspto-grants-2014_09
特許番号
US08822699B2

関連ノート

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