Hydrogen Peroxide → HCID 68513273, compound

HRID 2241260Notes

Reaction equation

HRID 2241260 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([CH:26]=[CH2:27])=[N:9]2)=[CH:5][CH:4]=1.B1C2CCCC1CCC2.[OH-:39].[Na+].OO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([CH2:26][CH2:27][OH:39])=[N:9]2)=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 685144684-(1-(4-methoxybenzyl)-3-vinyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

Product 1

HCID 68513273HCID 68513273, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-(1-(4-methoxybenzyl)-3-vinyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (1.17 g, 3.00 mmol) in THF (5 mL) was added 9-BBN (24.0 ml, 12.0 mmol, 0.5 M in THF). The reaction was stirred for 18 hours at room temperature. The reaction was chilled (submerged in an ice bath) and then quenched by addition of 5N aqueous sodium hydroxide (6.00 mL, 30.0 mmol). After stirring for 30 minutes in the ice bath, 30% aqueous hydrogen peroxide (2.88 mL, 30.0 mmol) was added. After stirring for 5 minutes at 0° C., the reaction was allowed to stir for 30 minutes at room temperature. The reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL). The phases were separated, and the aqueous phase was re-extracted with EtOAc (2×10 mL). The combined organic phases were washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated. The crude was purified by Biotage Flash 40M, eluting with 2% MeOH in DCM (2 L). The product was obtained as a waxy solid (1.0 g, 78%).

Workup

  1. temperatureThe reaction was chilled (submerged in an ice bath)
  2. additionwas added
  3. stirringAfter stirring for 5 minutes at 0° C.
  4. stirringto stir for 30 minutes at room temperature
  5. customThe reaction mixture was partitioned between water (20 mL) and EtOAc (20 mL)
  6. customThe phases were separated
  7. extractionthe aqueous phase was re-extracted with EtOAc (2×10 mL)
  8. washThe combined organic phases were washed with brine (20 mL)
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude was purified by Biotage Flash 40M
  13. washeluting with 2% MeOH in DCM (2 L)

Sources & evidence

ORD record
ord-60866504ef834c1382f18e96504223c8
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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