3-Pyridinylboronic acid → HCID 86700465, compound

HRID 879652Notes

Reaction equation

HRID 879652 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8](I)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1>>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([C:15]3[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=3)=[N:9][N:10]([CH3:11])[C:5]2=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 86700460HCID 86700460, compound

Product 1

HCID 86700465HCID 86700465, compound

Conditions

Temperature
70 °C

Procedure

To a solution of 5-chloro-3-iodo-1-methyl-1H-pyrazolo[4,3-b]pyridine (104 mg, 0.354 mmol, containing the isomer 5-chloro-3-iodo-2-methyl-21-1-pyrazolo[4,3-b]pyridine) was added pyridin-3-ylboronic acid (52 mg, 0.425 mmol). The reaction mixture was heated at 70° C. for 1 hr. Then the temperature was raised to 90° C. and the reaction was stirred at 90° C. for 2 h. The reaction was cooled down, washed with sat. NaHCO3, extracted with EtOAc, dried over MgSO4, filtered, concentrated down and purified by silica gel column to give the product. LCMS-ESI+: calc'd for C12H9ClN4: 245.0 (M+H+); Found: 245.3 (M+H+).

Workup

  1. temperatureThen the temperature was raised to 90° C.
  2. temperatureThe reaction was cooled down
  3. washwashed with sat. NaHCO3
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. custompurified by silica gel column
  9. customto give the product

Sources & evidence

ORD record
ord-94b38b3ac2e94df0b3eee3f8b8b04e14
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…