Tetrabutylammonium Fluoride → HCID 53250743, compound

HRID 1515648Notes

Reaction equation

HRID 1515648 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)(O)[CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][O: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:33]=[CH:34][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[CH2:27][CH2:26][CH2:25][O:24]2)=[CH:30][CH:31]=1)(=[O:36])=[O:37]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67228820HCID 67228820, compound

Product 1

HCID 53250743HCID 53250743, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-2-yl)-1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-ethanol (110 mg, 0.20 mmol) in tetrahydrofuran (0.5 mL) and a tetrabutylammonium fluoride solution in tetrahydrofuran (1 M, 2.0 mL, 2.0 mmol) was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate (150 mL), and washed with a saturated aqueous ammonium chloride solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo the residue was treated with methanol to afford 2-[(E)-1-(4-methanesulfonyl-phenyl)-2-(tetrahydro-furan-2-yl)-vinyl]-5-methoxy-1H-pyrrolo[2,3-b]pyridine (50 mg, 64.1%) as a light yellow solid: LC/MS m/e calcd for C21H22N2O4S [M+H]+ 399.48, observed 399.3; 1H NMR (400 MHz, CD3OD) δ ppm 8.05-8.09 (m, J=8.1 Hz, 2H), 7.94 (d, J=2.5 Hz, 1H), 7.60-7.64 (m, J=8.1 Hz, 2H), 7.43 (d, J=2.5 Hz, 1H), 6.46 (d, J=9.1 Hz, 1H), 5.86 (s, 1H), 4.11-4.24 (m, 1H), 3.97 (q, J=7.0 Hz, 1H), 3.85 (s, 3H), 3.73-3.81 (m, 1H), 3.22 (s, 3H), 2.03-2.13 (m, 2H), 1.79-1.97 (m, 2H).

Workup

  1. washwashed with a saturated aqueous ammonium chloride solution, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo the residue
  4. additionwas treated with methanol

Sources & evidence

ORD record
ord-84fef7b8dd144545bf0fa2f1ef1a59b3
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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