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

HRID 509968
ノート
印刷プレビュー

反応式

HRID 509968 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f9515dd36d224797bc2580365c9f45d5
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096593B2

反応ノート

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