Potassium Carbonate → HCID 123615096, compound

HRID 1771392Notes

Reaction equation

HRID 1771392 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10]([OH:13])=[N:11][CH:12]=2)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1.Br[CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[CH:9][C:10](=[O:13])[N:11]([CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:12]=2)[N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 178441178HCID 178441178, compound

Product 1

HCID 123615096HCID 123615096, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-(5-amino-3-(tert-butyl)-1H-pyrazol-1-yl)pyridin-2-ol (1.10 g, 4.74 mmol) in MeCN (10.0 mL) was added (2-bromoethoxy)(tert-butyl)dimethylsilane (1.28 mL, 5.68 mmol) and K2CO3 (0.785 g, 5.68 mmol) and the mixture heated to reflux for 6 hr. The resulting mixture was cooled and was loaded directly onto silica and purified by flash column chromatography (SiO2, 40 g, 0-100% EtOAc in isohexane, gradient elution) to afford the title compound, Intermediate A15, as a pale yellow solid (1.11 g, 60%); Rt 2.61 min (Method 2, acidic); m/z 391 (M+H)+, (ES+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 6 hr
  3. temperatureThe resulting mixture was cooled
  4. custompurified by flash column chromatography (SiO2, 40 g, 0-100% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-e83ae7a26ce54df181adf660f8929ffb
Source dataset
uspto-grants-2016_02
Patent number
US09249125B2

Reaction notes

Loading…