Water → HCID 178510055, compound

HRID 1952370Notes

Reaction equation

HRID 1952370 reaction equation
[O:1]=[C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([C:19]([F:22])([F:21])[F:20])[CH:5]=[CH:4][NH:3]1.Br[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[N:27](C(OC(C)(C)C)=O)[N:26]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[O:1]=[C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([C:19]([F:20])([F:22])[F:21])[CH:5]=[CH:4][N:3]1[CH2:24][C:25]1[C:33]2[C:28](=[N:29][CH:30]=[CH:31][CH:32]=2)[NH:27][N:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylateHCID 70839153HCID 70839153, compound

Product 1

HCID 178510055HCID 178510055, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-{[2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl]oxy}isophthalonitrile (0.076 g, 0.249 mmol), tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (0.078 g, 0.249 mmol) and potassium carbonate (0.034 g, 0.249 mmol) were combined and diluted with dimethylformamide (1 mL) and stirred at room temperature. After 16 hours, water (10 mL) was added and the mixture was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with brine (3×25 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting solid was dissolved in TFA. After 30 minutes, the solution was concentrated. The resulting solid was suspended in methanol and filtered to afford the title compound as a solid. 1H NMR (DMSO-d6) δ 8.52 (d, J=4.6 Hz, 1H), 8.17-8.17 (m, 1H), 8.15 (d, J=8.2 Hz, 1H), 8.06 (d, J=7.1 Hz, 1H), 7.98 (m, 2H), 7.18 (dd, J=8.2 Hz, J=4.7 Hz, 1H), 6.65 (d, J=7.3 Hz, 1H), 5.52 (s, 2H). HRMS (M+1)=437.0981.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2×25 mL)
  2. washThe combined organic extracts were washed with brine (3×25 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. dissolutionThe resulting solid was dissolved in TFA
  7. waitAfter 30 minutes
  8. concentrationthe solution was concentrated
  9. filtrationfiltered

Sources & evidence

ORD record
ord-826a215787e8475c8131f4c40e487635
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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