Tetrabutylammonium Fluoride → 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1515624Notes

Reaction equation

HRID 1515624 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][CH:20]4[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[O:21]4)[CH:18]=[C:13]3[CH:12]=[C:11]2[C:27]([C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)=[CH:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH:29]1([CH:28]=[C:27]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([CH2:19][CH:20]4[CH2:24][O:23][C:22]([CH3:25])([CH3:26])[O:21]4)[CH:18]=[C:13]3[CH:12]=2)[C:34]2[CH:39]=[CH:38][C:37]([S:40]([CH3:43])(=[O:42])=[O:41])=[CH:36][CH:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672288531-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672286442-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridineYield 88.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (460 mg, 0.74 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 4 mL, 4 mmol) was stirred at room temperature for 12 h. The mixture was diluted with ethyl acetate (150 mL) and then washed with a saturated aqueous ammonium chloride solution, brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (315 mg, 88.5%) as a light yellow solid: LC/MS m/e calcd for C27H32N2O4S [M+H]+ 481.63, observed 481.1.

Workup

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

Sources & evidence

ORD record
ord-f56eeb7da00b4f929af7932e0892b557
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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