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Sodium hydride → 3-[4-(1-carbomethoxy-1-(3-chlorophenyl)methoxy)-3-chloro-5-propylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine

HRID 1492643
ノート
印刷プレビュー

反応式

HRID 1492643 の反応式
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:11][CH3:12])[NH:10][C:5]2=[C:4]([CH3:13])[CH:3]=1.[H-].[Na+].[Cl:16][C:17]1[CH:35]=[C:34]([CH2:36]O)[CH:33]=[C:32]([CH2:38][CH2:39][CH3:40])[C:18]=1[O:19][CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[C:21]([CH:20]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[O:19][C:18]1[C:32]([CH2:38][CH2:39][CH3:40])=[CH:33][C:34]([CH2:36][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:13])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:35][C:17]=1[Cl:16])([O:23][CH3:24])=[O:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 54026416Methyl 2-(2-chloro-4-hydroxymethyl-6-propyl-phenoxy)-2-(3-chlorophenyl)acetate

生成物 1

HCID 543926843-[4-(1-carbomethoxy-1-(3-chlorophenyl)methoxy)-3-chloro-5-propylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine収率 58%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

実験手順

To a solution of 0.085 g (0.49 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine in 1.0 mL anhydrous DMF was added 21.0 mg (0.54 mmol) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under a nitrogen atmosphere at room temperature for 1 hour. A solution of 0.250 g (0.56 mmol) of the product of Step C in 0.5 mL of DMF was added and the reaction was stirred an additional 2 hours at room temperature. The reaction mixture was partitioned between EtOAc and water, separated, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 50% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 0.150 g (58%) of the title compound.

後処理

  1. stirringthe reaction was stirred an additional 2 hours at room temperature
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customseparated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 50% EtOAc-hexane
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

出典と根拠

ORDレコード
ord-8ec98483b3924366baa035813fa55002
出典データセット
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05374638

反応ノート

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