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

HRID 509968
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HRID 509968 반응식
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH:20]([C:22]3[CH:23]=[N:24][C:25]([N:28]4[Si](C)(C)CC[Si]4(C)C)=[CH:26][CH:27]=3)O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1N=CC(C(C2C3C(=NC=C(Cl)C=3)N(S(C3C=CC=CC=3)(=O)=O)C=2)O)=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Cl:19])[CH:18]=[C:13]3[C:12]([CH2:20][C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[N:24][CH:23]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57619405alpha-(6-Amino-3-pyridinyl)-5-chloro-1-(phenylsulfonyl)-1H-pyrrolo(2,3-b)pyridine-3-methanolHCID 67200889(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-(2,2,5,5-tetramethyl-[1,2,5]azadisilolidin-1-yl)-pyridin-3-yl]-methanol

생성물 1

HCID 57619223
2-Pyridinamine, 5-[[5-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]methyl]-

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To (1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-[6-(2,2,5,5-tetramethyl-[1,2,5]azadisilolidin-1-yl)-pyridin-3-yl]-methanol and (6-amino-pyridin-3-yl)-(1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanol (118, 119, 1.70/1.25 g mix, 2.41 mmol) in 25.0 mL of dichloromethane, triethylsilane (3.00 mL, 18.8 mmol) and trifluoroacetic acid (1.50 mL, 19.5 mmol) were added and the reaction stirred at room temperature overnight. The reaction was concentrated under vacuum, combined with aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 20-100% ethyl acetate in hexane to provide the desired compound (120, 0.70 g).

후처리

  1. concentrationThe reaction was concentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 20-100% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-f9515dd36d224797bc2580365c9f45d5
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096593B2

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