Cesium carbonate → HCID 67470406, compound

HRID 1522649Notes

Reaction equation

HRID 1522649 reaction equation
[I:1][C:2]1[C:3]2[C:4](=[CH:8][NH:9][N:10]=2)[N:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[N:9][N:10]([CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[C:3]=12

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 106071724-Bromo-2-methylbutan-2-olHCID 178506553HCID 178506553, compound

Product 1

HCID 67470406HCID 67470406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (357 mg, 1.457 mmol), 4-bromo-2-methylbutan-2-ol (243 mg, 1.457 mmol) and Cs2CO3 (475 mg, 1.457 mmol) were combined in DMF (5 mL) and heated in a microwave at 120° C. for 40 minutes. The reaction was then cooled, filtered, and concentrated to give a residue which was purified by silica chromatography eluted with a step gradient of EtOAc in hexanes to give 4-(7-iodo-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylbutan-2-ol which was dried and used immediately.

Workup

  1. temperatureThe reaction was then cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give a residue which
  5. customwas purified by silica chromatography
  6. washeluted with a step gradient of EtOAc in hexanes

Sources & evidence

ORD record
ord-b417fc0ff044424ba675e43a6d18f861
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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