Tetrabutylammonium Fluoride → HCID 53251250, compound

HRID 1515708Notes

Reaction equation

HRID 1515708 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)([OH:27])[CH2:21][CH:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:22]1([CH2:21][C:20]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=2)([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)[OH:27])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67228387HCID 67228387, compound

Product 1

HCID 53251250HCID 53251250, compoundYield 2.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethanol (5.1 g, 9.4 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 20 mL, 20 mmol) was stirred at room temperature for 2 h. The mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification using a Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 2-cyclopentyl-1-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-(4-methanesulfonyl-phenyl)-ethanol (100 mg) as a white solid: LC/MS m/e calcd for C21H23FN2O3S [M+H]+ 403.49, observed 403.1; 1H NMR (400 MHz, CD3OD) δ ppm 8.11 (br. s., 1H), 7.95-8.00 (m, J=8.3 Hz, 2H), 7.88-7.94 (m, J=8.6 Hz, 2H), 7.77 (dd, J=9.1, 2.3 Hz, 1H), 6.60 (s, 1H), 3.16-3.23 (m, 3H), 2.54-2.64 (m, 2H), 1.83-1.98 (m, 2H), 1.43-1.71 (m, 5H), 1.25-1.40 (m, 1H), 1.05-1.15 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-3b4a0358f059442594ca0b63eeaeeed1
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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