Tetrabutylammonium Fluoride → HCID 67228346, compound

HRID 1515665Notes

Reaction equation

HRID 1515665 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]([C:35]([F:38])([F:37])[F: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>[CH3:20][O:19][C:17]1[CH:18]=[C:13]2[CH:12]=[C:11]([C:21]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=3)=[CH:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)[NH:10][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67228618HCID 67228618, compound

Product 1

HCID 67228346HCID 67228346, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-benzenesulfonyl-5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1-(4-trifluoromethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (260 mg, 0.48 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 5-methoxy-2-[2-(tetrahydro-pyran-4-yl)-1-(4-trifluoromethyl-phenyl)-vinyl]-1H-pyrrolo[2,3-b]pyridine (193 mg, quant.) as a white solid: LC/MS m/e calcd for C22H21F3N2O2 [M+H]+ 403.42, observed 403.2.

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-1b44ee58d8a94a628b7e96c9dc582051
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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