Tetrabutylammonium Fluoride → HCID 59331537, compound

HRID 1882013Notes

Reaction equation

HRID 1882013 reaction equation
[Si]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:18][C:19]([CH:23]([C:31]3[CH:36]=[CH:35][C:34]([S:37]([CH:40]4[CH2:42][CH2:41]4)(=[O:39])=[O:38])=[CH:33][CH:32]=3)[CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[CH:20][C:21]=2[CH3:22])=[N:15][CH:16]=1)[CH3:10])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:40]1([S:37]([C:34]2[CH:33]=[CH:32][C:31]([CH:23]([C:19]3[NH:18][C:17]([C:14]4[N:15]=[CH:16][C:11]([CH:9]([OH:8])[CH3:10])=[CH:12][CH:13]=4)=[C:21]([CH3:22])[CH:20]=3)[CH2:24][CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)=[CH:36][CH:35]=2)(=[O:39])=[O:38])[CH2:42][CH2:41]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 593315955-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridine

Product 1

HCID 59331537HCID 59331537, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution (5 mL) of 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridine (130 mg) in tetrahydrofuran (5 mL) was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 256 μL), and the mixture was stirred overnight at room temperature. 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 (83.0 mg, yield 79%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (3:1, volume ratio). MS: 495 (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-c753f7371be24fda94c92454b03d4c2d
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…