Cesium carbonate → HCID 67469571, compound

HRID 1522645Notes

Reaction equation

HRID 1522645 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[C:3]2[C:4](=[CH:8][N:9]([CH2:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])[N:10]=2)[N:5]=[CH:6][CH:7]=1.[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

6

Reactant 3

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

Product 2

HCID 67469571HCID 67469571, compoundHCID 67470406HCID 67470406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (342 mg, 1.396 mmol), 4-bromo-2-methylbutan-2-ol (233 mg, 1.396 mmol) and Cs2CO3 (455 mg, 1.396 mmol) were combined in DMF (5 mL) and heated in a microwave at 120° C. for 60 minutes. The reaction was cooled, filtered, and concentrated to give a residue which purified on a silica column and eluted using a step gradient of EtOAc (0-90%) in hexanes to give 4-(7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylbutan-2-ol and 4-(7-iodo-1H-pyrazolo[4,3-b]pyridin-1-yl)-2-methylbutan-2-ol.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customto give a residue which
  5. custompurified on a silica column
  6. washeluted

Sources & evidence

ORD record
ord-6409fe6b14bb4bd7bced035722f68994
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

Loading…