Pyridine → HCID 59261368, compound

HRID 422542Notes

Reaction equation

HRID 422542 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:17])([CH3:16])[C:13]([CH3:19])([CH3:18])[O:12]1.S(Cl)(Cl)=O.[CH3:24][N:25]1[C:29]([NH2:30])=[CH:28][CH:27]=[N:26]1.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:30][C:29]2[N:25]([CH3:24])[N:26]=[CH:27][CH:28]=2)=[O:8])=[CH:4][C:3]=1[B:11]1[O:15][C:14]([CH3:16])([CH3:17])[C:13]([CH3:19])([CH3:18])[O:12]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 160860864-Methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Product 1

HCID 59261368HCID 59261368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottomed flask was added 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (2.0 g, 7.6 mmol) and thionyl chloride (14 ml, 191 mmol) and the reaction mixture was stirred at RT for 1 h. Excess thionyl chloride was evaporated under vacuum and the remaining trace amount was removed azeotropically by addition of toluene (5 mL) and repeated concentration under reduced pressure. To the resulting residue was added DCM (10 mL) followed by 1-methyl-1H-pyrazol-5-amine (1.1 g, 11 mmol) and pyridine (1.2 ml, 15 mmol). The reaction was stirred at reflux for 1 h then cooled to RT. The mixture was diluted with DCM, washed with water followed by sat. NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. The brown residue was loaded on an ISCO 40 g column (eluted with 25-65% EtOAc in Hexanes) and purified to provide the title compound as an off-white amorphous solid. MS (ESI, pos. ion) m/z: 342.2 (M+1).

Workup

  1. customExcess thionyl chloride was evaporated under vacuum
  2. customthe remaining trace amount was removed azeotropically by addition of toluene (5 mL)
  3. concentrationconcentration under reduced pressure
  4. additionTo the resulting residue was added DCM (10 mL)
  5. stirringThe reaction was stirred
  6. temperatureat reflux for 1 h
  7. temperaturethen cooled to RT
  8. washwashed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. washThe brown residue was loaded on an ISCO 40 g column (eluted with 25-65% EtOAc in Hexanes)
  13. custompurified

Sources & evidence

ORD record
ord-9e87c82171f84bee9a702e472508359e
Source dataset
uspto-grants-2012_01
Patent number
US08101612B2

Reaction notes

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