Tetrahydrofuran → HCID 67228577, compound

HRID 1515872Notes

Reaction equation

HRID 1515872 reaction equation
C1(S([N:10]2[C:14]3=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][CH:29]=2)=[CH:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl-].[Na+].O>[CH:23]1([CH:22]=[C:21]([C:11]2[NH:10][C:14]3=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=[C:13]3[CH:12]=2)[C:28]2[CH:29]=[CH:30][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:32][CH:33]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67229612HCID 67229612, compound

Product 1

HCID 67228577HCID 67228577, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (300 mg, 0.56 mmol) and tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 20 mL, 20 mmol) was stirred for 12 h at 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 give 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-vinyl]-6-methoxy-1H-pyrrolo[2,3-b]pyridine (0.22 g, 100%) as a solid which was used in the next step without purification: LC/MS m/e calcd for C22H24N2O3S [M+H]+ 397.51, observed 397.2.

Workup

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

Sources & evidence

ORD record
ord-b1c07e82477246ee88735531399fd36f
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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