Water → 4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253542Notes

Reaction equation

HRID 1253542 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][CH:18]=2)[CH:12]=[C:13](Br)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([N:16]=[CH:17][CH:18]=2)[CH:12]=[C:13]([C:23]2[CH:22]=[N:21][N:20]([CH3:19])[CH:24]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 673757094-(Benzyloxy)-6-bromopyrazolo[1,5-a]pyridine

Product 1

HCID 673749564-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4-(benzyloxy)-6-bromopyrazolo[1,5-a]pyridine (200 mg, 0.660 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (412 mg, 1.979 mmol), tetrakis(triphenylphosphine)palladium (0) (76 mg, 0.066 mmol), and sodium carbonate (210 mg, 1.98 mmol) were suspended in 1,4-dioxane (4 ml)/water (0.444 ml). The mixture was sparged with argon for 10 minutes, then heated to 90° C. for 2 h. After cooling to ambient temperature, the reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to afford 4-(benzyloxy)-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine contaminated with triphenylphosphine oxide.

Workup

  1. customThe mixture was sparged with argon for 10 minutes
  2. temperatureAfter cooling to ambient temperature
  3. additionthe reaction mixture was diluted in ethyl acetate
  4. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-2afdcd5abb26445d9669a7c58d6a6c61
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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