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

HRID 1515658Notes

Reaction equation

HRID 1515658 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-513c756e908f4734bb7831912ba2bbbe
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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