Tetrabutylammonium Fluoride → HCID 67228192, compound

HRID 1515662Notes

Reaction equation

HRID 1515662 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:21]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)=[CH:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:38][S:35]([C:32]1[CH:31]=[CH:30][C:29]([C:21]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=[C:13]3[CH:12]=2)=[CH:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:34][CH:33]=1)(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67229023HCID 67229023, compound

Product 1

HCID 67228192HCID 67228192, compoundYield 80.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzenesulfonyl-2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (300 mg, 0.54 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 2 mL, 2 mmol) was stirred at room temperature for 12 h. The resulting mixture was diluted with ethyl acetate (150 mL), washed with a saturated aqueous ammonium chloride solution and brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 2-[1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-pyran-4-yl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (180 mg, 80.7%) as a white solid: LC/MS m/e calcd for C22H24N2O4S [M+H]+ 413.54, observed 413.1.

Workup

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

Sources & evidence

ORD record
ord-babdda62bd3145fca44789996f247e85
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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