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

HRID 8819
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HRID 8819 반응식
[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]
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참가 물질

5

반응물 2

HCID 2733832Lithium hexamethyldisilazaneHCID 219849482-[(Tert-butylsulfonyl)methoxy]-6-(2-chlorophenyl)-5-(4-chlorophenyl)-nicotinonitrile

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8aaed631857a4993a8ca04b643cc93d8
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07091216B2

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