Tetrahydrofuran → HCID 67227886, compound

HRID 1515906Notes

Reaction equation

HRID 1515906 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH2:21][CH3:22])=[O:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:23]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH:25]1([CH:24]=[C:23]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([S:19]([CH2:21][CH3:22])=[O:20])[CH:18]=[C:13]3[CH:12]=2)[C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 672293991-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67227886HCID 67227886, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridine (56 mg, 0.096 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 3.85 mL, 3.85 mmol) was stirred for 12 h at room temperature. The mixture was poured into brine (5 mL), extracted with ethyl acetate (2×20 mL), washed with a saturated aqueous ammonium chloride solution (3×10 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to give 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-ethanesulfinyl-1H-pyrrolo[2,3-b]pyridine (37 mg, 88%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C23H26N2O3S2 [M+H]+ 443.6, observed 443.1.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×10 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-349b26d989c949229afd371182881a0c
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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