Tetrahydrofuran → HCID 67228582, compound

HRID 1515864Notes

Reaction equation

HRID 1515864 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][N:28]=2)(O)[CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH:21]1([CH:20]=[C:19]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=2)[C:27]2[CH:32]=[CH:31][C:30]([S:33]([CH3:36])(=[O:35])=[O:34])=[CH:29][N:28]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67228469HCID 67228469, compound

Product 1

HCID 67228582HCID 67228582, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-cyclopentyl-1-(5-methanesulfonyl-pyridin-2-yl)-ethanol (0.12 g, 0.23 mmol) and tetrabutylammonium fluoride in tetrahydrofuran (1 M, 4.6 mL, 4.6 mmol) was stirred for 3 h at room temperature. After cooling to room temperature, the mixture was poured into brine (15 mL), extracted with ethyl acetate (2×100 mL), washed with a saturated aqueous ammonium chloride solution (3×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[2-cyclopentyl-1-(5-methanesulfonyl-pyridin-2-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (84 mg, 100%) which was used in the next step without purification: LC/MS m/e calcd for C20H21N3O2S [M+H]+ 368.47, observed 368.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with a saturated aqueous ammonium chloride solution (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c046cb589d3b40f0a4e2aab153321b4b
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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