Tetrabutylammonium Fluoride → HCID 178489413, compound

HRID 1865595Notes

Reaction equation

HRID 1865595 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[N:18][N:17](COCC[Si](C)(C)C)[C:14]3=[N:15][CH:16]=2)[CH:8]=[N:7][CH:6]=1)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([C:9]3[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=3)[C:4]([OH:36])=[O:3])[CH:12]=2)[NH:17][N:18]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 598360525-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid ethyl ester

Product 1

HCID 178489413HCID 178489413, compoundYield 192.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid ethyl ester (494 mg, 0.98 mmol) in THF (20 mL) was added tetra-n-butylammonium fluoride in THF (1M, 10 ml, 10 mmol) and activated 4 Å molecular sieves. The resulting mixture was stirred at 70° C. for 7 h. The sieves were filtered off, washing with ethyl acetate and the resulting filtrate concentrated. The residue was distributed between dichloromethane and water. The aqueous phase was extracted three times with dichloromethane and the organic phases combined, dried over sodium sulfate, filtered and concentrated to afford of 5-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-nicotinic acid (654 mg, 62% purity, 405 mg, 119% yield) as a brown solid. 1H-NMR (500 MHz, d6-DMSO) δ 13.98 (s, 1H), 8.99 (d, 1H), 8.95 (s, 1H), 8.88 (d, 1H), 8.43 (t, 1H), 8.40 (d, 1H), 7.67 (dd, 1H), 7.47 (ddd, 1H), 7.23 (d, 1H), 7.10 (dt, 1H), 3.86 (s, 3H). MS: m/z 345 (96%) [M−H−].

Workup

  1. filtrationThe sieves were filtered off
  2. washwashing with ethyl acetate
  3. concentrationthe resulting filtrate concentrated
  4. extractionThe aqueous phase was extracted three times with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a4cd4a8d9977423d817e8ed6e7292d3d
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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