Tetrabutylammonium Fluoride → HCID 59331287, compound

HRID 1881999Notes

Reaction equation

HRID 1881999 reaction equation
[Si]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[C:22]([C:26]2[NH:27][C:28]([CH:31]([C:39]3[CH:44]=[CH:43][C:42]([S:45]([CH3:48])(=[O:47])=[O:46])=[CH:41][CH:40]=3)[CH2:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][CH:30]=2)[CH:21]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:48][S:45]([C:42]1[CH:43]=[CH:44][C:39]([CH:31]([C:28]2[NH:27][C:26]([C:22]3[CH:21]=[C:20]([CH2:19][OH:18])[CH:25]=[CH:24][N:23]=3)=[CH:30][CH:29]=2)[CH2:32][CH:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)=[CH:40][CH:41]=1)(=[O:47])=[O:46]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59331624HCID 59331624, compound

Product 1

HCID 59331287HCID 59331287, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-(5-{1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine (870 mg) in tetrahydrofuran (10 mL) was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 1.54 mL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (533 mg, yield 95%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate. MS: 441 (MH+).

Workup

  1. washwashed with water
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-139765a169ee497f829f2e39e9f23d0a
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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