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Trifluoroacetic acid → 2-Pyridinamine, 5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-

HRID 1024286
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HRID 1024286 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([Cl:19])[CH:17]=3)[N:12]([S:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:11]=2)O)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:23]1([S:20]([N:12]2[C:13]3=[N:14][CH:15]=[C:16]([Cl:19])[CH:17]=[C:18]3[C:10]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][CH:6]=3)=[CH:11]2)(=[O:22])=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57619405alpha-(6-Amino-3-pyridinyl)-5-chloro-1-(phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-3-methanol

생성물 1

HCID 576192232-Pyridinamine, 5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

To (6-amino-pyridin-3-yl)-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (598, 1.00 g, 0.00241 mol) in dichloromethane (25.0 mL) were added triethylsilane (3.00 mL, 0.0188 mol) and trifluoroacetic acid (1.50 mL, 0.0195 mol). The reaction was stirred at room temperature overnight, then concentrated, poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (599, 0.70 g, 73%).

후처리

  1. concentrationconcentrated
  2. additionpoured into aqueous potassium carbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% to 100% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-d914d42095684b19930f5f681f82bb54
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08722702B2

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