Tetrabutylammonium Fluoride → Benzamide

HRID 1515690Notes

Reaction equation

HRID 1515690 reaction equation
C1(S(N2C3=NC=CC=C3C=C2C([C:26]2[CH:38]=[CH:37][C:29]([C:30]([NH:32]C(C)(C)C)=[O:31])=[CH:28][CH:27]=2)=CC2CCCC2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:30]([NH2:32])(=[O:31])[C:29]1[CH:37]=[CH:38][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672285854-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-N-tert-butyl-benzamide

Product 1

HCID 2331BenzamideYield 318.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-vinyl]-N-tert-butyl-benzamide (300 mg, 0.57 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 5 mL, 5 mmol) was stirred at room temperature for 12 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 to afford N-tert-butyl-4-[2-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-vinyl]-benzamide (220 mg, quant.) as a white solid: LC/MS m/e calcd for C25H29N3O [M+H]+ 388.53, observed 388.2.

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-45aa8d726c7f4581972a9e85e8c1f8c6
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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