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Ethyl{[6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl]oxy}acetate → Ethyl 3-amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridine-2-carboxylate

HRID 8820
ノート
印刷プレビュー

反応式

HRID 8820 の反応式
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[C:12]([C:13]#[N:14])=[CH:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])[N:8]=1)[CH3:2].C[Si]([NH-])(C)C.C[Si]([NH-])(C)C.[Li+].[Li+]>CN(C=O)C.C1COCC1>[NH2:14][C:13]1[C:12]2[C:7](=[N:8][C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH:11]=2)[O:6][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:29]
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 2

HCID 21984952Ethyl{[6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl]oxy}acetateHCID 86588160Lithim bis(trimethylsilylamide)

生成物 1

HCID 21984925Ethyl 3-amino-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridine-2-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a magnetically stirred solution of 2.69 g (6.30 mmol) of the product of Step A dissolved in 60 mL of DMF was slowly added 12.6 mL of a 1 M solution of lithium bis(trimethylsilylamide) in THF at 0° C. The reaction mixture was stirred at room temperature for 20 min then partitioned between EtOAc and 10% aq. NaHSO4. The organic extracts were separated, washed with 10% aq. NaHSO4, brine, dried (Na2SO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound. HPLC/MS: 427.0 (M+1), 428.9 (M+3); Rt=4.03 min.

後処理

  1. customat 0° C
  2. customthen partitioned between EtOAc and 10% aq. NaHSO4
  3. customThe organic extracts were separated
  4. washwashed with 10% aq. NaHSO4, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on a silica gel flash chromatography column
  9. washeluted with 0–20% EtOAc-hexane
  10. customEvaporation of the purified fractions
  11. customdrying in vacuo

出典と根拠

ORDレコード
ord-0072402313da45f9b61c45596ccdd4e7
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091216B2

反応ノート

読み込み中…

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