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Lithium hexamethyldisilazane → 2-(Tert-butylsulfonyl)-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-3-amine

HRID 8819
ノート
印刷プレビュー

反応式

HRID 8819 の反応式
[C:1]([S:5]([CH2:8][O:9][C:10]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:15]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:14][C:11]=1[C:12]#[N:13])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>CN(C=O)C.C1COCC1>[C:1]([S:5]([C:8]1[O:9][C:10]2=[N:17][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])=[C:15]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)[CH:14]=[C:11]2[C:12]=1[NH2:13])(=[O:6])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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 2733832Lithium hexamethyldisilazaneHCID 219849482-[(Tert-butylsulfonyl)methoxy]-6-(2-chlorophenyl)-5-(4-chlorophenyl)-nicotinonitrile

生成物 1

HCID 219848092-(Tert-butylsulfonyl)-6-(2-chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-3-amine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 1.87 g (3.9 mmol) of the product of Step B in 24 mL of DMF at 0° C. was added 7.9 mL of a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF. The reaction mixture was stirred an addition 5 min then it was quenched with 0.45 mL of acetic acid and then partitioned between ethyl acetate and saturated NaCl solution. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then purified via silica gel flash chromatography eluting with a gradient of 0 to 40% ethyl acetate/hexane to afford the title compound. HPLC/MS: 475.1 (M+1), 477.0 (M+3); Rt=3.99 min.

後処理

  1. additionan addition 5 min
  2. customit was quenched with 0.45 mL of acetic acid
  3. custompartitioned between ethyl acetate and saturated NaCl solution
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified via silica gel flash chromatography
  9. washeluting with a gradient of 0 to 40% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-8aaed631857a4993a8ca04b643cc93d8
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

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