Tetrahydrofuran → HCID 67228774, compound

HRID 1515916Notes

Reaction equation

HRID 1515916 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F: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]([C:19]([F:21])([F:22])[F:20])[CH:18]=[C:13]3[CH:12]=2)[C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:32][CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 672286611-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 67228774HCID 67228774, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (270 mg, 0.47 mmol) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1 M, 9.4 mL, 9.4 mmol) was stirred for 12 h at room temperature. The mixture was poured into brine (15 mL), extracted with ethyl acetate (2×50 mL), washed with a saturated aqueous ammonium chloride solution (3×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (190 mg, 93%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C22H21F3N2O2S [M+H]+ 435.48, observed 434.8.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with a saturated aqueous ammonium chloride solution (3×20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b39275a894cc425d86be97454d6800a6
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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