Potassium Acetate → 4-chloro-6-(1H-indazol-5-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

HRID 241951Notes

Reaction equation

HRID 241951 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]2[N:9]([CH3:12])[N:10]=[CH:11][C:3]=12.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)O1.C([O-])(=O)C.[K+]>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][N:25]=[CH:24]3)[N:5]=[C:4]2[N:9]([CH3:12])[N:10]=[CH:11][C:3]=12

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 177504691H-Indazole-5-boronic acid pinacol esterHCID 580832354,6-dichloro-1-methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 580832414-chloro-6-(1H-indazol-5-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4,6-Dichloro-1-methyl-1H-pyrazolo[3,4-b]pyridine 5 (0.180 g, 0.89 mmol) was dissolved in 2 mL dioxane and 2 mL acetonitriile in a microwave tube, and nitrogen was bubbled through the solution. 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (0.217 g, 0.89 mmol) and a 1M solution of potassium acetate (2 mL, 2 mmol) were added. Nitrogen gas was bubbled through the mixture followed by the addition of 5 mole % of tetrakis(triphenylphosphine) palladium (0). The resultant mixture was microwaved at 125° C. for 30 minutes. Purification via Biotage reverse phase system (4:1 ethyl acetate/hexanes) gave 12.

Workup

  1. custom2 mL acetonitriile in a microwave tube, and nitrogen was bubbled through the solution
  2. customNitrogen gas was bubbled through the mixture
  3. additionfollowed by the addition of 5 mole % of tetrakis(triphenylphosphine) palladium (0)
  4. customThe resultant mixture was microwaved at 125° C. for 30 minutes
  5. customPurification via Biotage

Sources & evidence

ORD record
ord-fdb1ec330209459f807057b44e9c4595
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

Loading…