Tetrabutylammonium Fluoride → HCID 16035849, compound

HRID 222298Notes

Reaction equation

HRID 222298 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:30]=[CH:29][C:18]3=[N:19][CH:20]=[C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:22]=[C:17]3[C:16](=[O:31])[C:15]=2[CH:32]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:30]=[CH:29][C:18]3=[N:19][CH:20]=[C:21]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:22]=[C:17]3[C:16](=[O:31])[C:15]=2[CH:32]=1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57722842HCID 57722842, compound

Product 1

HCID 16035849HCID 16035849, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

7-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(1-methyl-1H-pyrazol-4-yl)-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (5 mg, 0.011 mmol) was dissolved in 0.5 mL of tetrahydrofuran. Tetrabutylammonium fluoride (0.013 mL of 1.0M in THF, 0.013 mmol) was added and the mixture was stirred at room temperature for 1 hour. The reaction was diluted with ethyl acetate and brine and washed with brine twice. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via reverse phase HPLC (10-70% acetonitrile/water gradient, 0.05% trifluoroacetic acid modifier) afforded the title compound. 1H NMR (600 MHz, CDCl3) δ 9.01 (d, 1H); 8.58 (s, 1H); 8.16 (d, 1H); 7.92 (s, 1H); 7.81 (s, 1H); 7.59 (dd, 1H); 7.56 (d, 1H); 7.35 (d, 1H); 7.24 (d, 1H); 3.99 (s, 3H); 3.96 (t, 2H); 3.03 (t, 2H). Hydroxyl proton was not observed. LRMS (APCI) calc'd for (C20H18N3O2) [M+H]+, 332.1; found 332.1.

Workup

  1. washwashed with brine twice
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification via reverse phase HPLC (10-70% acetonitrile/water gradient, 0.05% trifluoroacetic acid modifier)

Sources & evidence

ORD record
ord-81cd81ce3a924166837a5d063c86f77a
Source dataset
uspto-grants-2012_06
Patent number
US08207186B2

Reaction notes

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