Cesium carbonate → methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

HRID 1471756Notes

Reaction equation

HRID 1471756 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16]2[NH:20][N:19]=[CH:18][CH:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C>[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16]2[CH:17]=[CH:18][N:19]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])[N:20]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 76934Methyl 3-bromopropanoateHCID 866907933-((tert-butyldimethylsilyloxy)methyl)-2-(1H-pyrazol-5-yl)pyridine

Product 1

HCID 86690794methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoateYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-((tert-butyldimethylsilyloxy)methyl)-2-(1H-pyrazol-5-yl)pyridine (140 mg, 0.48 mmol, 1 eq.) and Cs2CO3 (312 mg, 0.96 mmol, 2 eq.) in DMF (3 mL) was added methyl 3-bromopropanoate (122 mg, 0.73 mmol, 1.5 eq.). The mixture was stirred at rt for 6 h, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate (110 mg, 61%). LRMS (M+H+) m/z 376.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified on silica gel using
  4. additiona mixture of EtOAc and hexanes as eluent

Sources & evidence

ORD record
ord-6399a7dfea364768893fdac1d5e36d8a
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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