Tetrabutylammonium Fluoride → 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol

HRID 1515658ノート

反応式

HRID 1515658 の反応式
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH2:20][CH2:21][O:22][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:40]([C:47]2[CH:52]=[CH:51][C:50]([S:53]([CH3:56])(=[O:55])=[O:54])=[CH:49][CH:48]=2)=[CH:41][CH:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:42]1([CH:41]=[C:40]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([O:19][CH2:20][CH2:21][OH:22])[CH:18]=[C:13]3[CH:12]=2)[C:47]2[CH:52]=[CH:51][C:50]([S:53]([CH3:56])(=[O:55])=[O:54])=[CH:49][CH:48]=2)[CH2:46][CH2:45][CH2:44][CH2:43]1

参加物

5

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 672286821-benzenesulfonyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 672286052-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol収率 99.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 1-benzenesulfonyl-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethoxy]-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (870 mg, 1.08 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 10 mL, 10 mmol) was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-yloxy}-ethanol (460 mg, quant.) as a white solid: LC/MS m/e calcd for C23H26N2O4S [M+H]+ 427.54, observed 427.4.

後処理

  1. washwashed with a saturated aqueous ammonium chloride solution and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-513c756e908f4734bb7831912ba2bbbe
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

反応ノート

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