Tetrabutylammonium Fluoride → HCID 59853084, compound

HRID 1670332Notes

Reaction equation

HRID 1670332 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[N:12][CH:13]=[CH:14][C:15]=1[O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([C:26]2[C:27](=[O:39])[N:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:29]=[CH:30][CH:31]=2)=[O:25])=[CH:19][C:18]=1[F:40])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[F:40][C:18]1[CH:19]=[C:20]([NH:23][C:24]([C:26]2[C:27](=[O:39])[N:28]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[CH:29]=[CH:30][CH:31]=2)=[O:25])[CH:21]=[CH:22][C:17]=1[O:16][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:45])([CH3:46])[CH3:47])[C:10]=1[CH2:9][OH:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59852928HCID 59852928, compound

Product 1

HCID 59853084HCID 59853084, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To tert-Butyl 3-((tert-butyldimethylsilyloxy)methyl)-4-(2-fluoro-4-(1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamido)phenoxy)pyridin-2-ylcarbamate (119 mg, 0.176 mmol) in THF (2 mL) at rt was added tetrabutylammonium fluoride (260 μL, 0.264 mmol, 1 M in THF). After stirring at rt for 30 min, the reaction was diluted with ethyl acetate (20 mL), washed with water followed by brine (10 mL each), dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (5% MeOH/EtOAc) to give the title compound (66 mg, 66%) as a yellow oil. 1H NMR (CD3OD) δ 8.62 (dd, 1H, J=7.2, 2 Hz), 8.04 (d, 1H, J=6 Hz), 7.94-7.90 (m, 2H), 7.50-7.46 (m, 2H), 7.33-7.25 (m, 3H), 7.20 (t, 1H, J=8.8 Hz), 6.67 (t, 1H, J=6.8 Hz), 6.40 (d, 1H, J=5.2 Hz), 4.78 (s, 2H), 1.49 (s, 9H); MS (ESI+) m/z 565.17 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography on silica gel (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-fbeb66609ed746b78009b2fbed64801e
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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