Cesium carbonate → HCID 67469562, compound

HRID 1522575Notes

Reaction equation

HRID 1522575 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.Cl[CH2:12][C:13]([CH3:16])([OH:15])[CH3:14].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][C:13]([CH3:16])([OH:15])[CH3:14])[N:10]=2)[N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 178506553HCID 178506553, compound

Product 1

HCID 67469562HCID 67469562, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7-Iodo-2H-pyrazolo[4,3-b]pyridine (300 mg, 1.224 mmol), 1-chloro-2-methylpropan-2-ol (133 mg, 1.224 mmol) and Cs2CO3 (399 mg, 1.224 mmol) were combined in DMF (5 mL). The mixture was heated at 120° C. for 30 minutes using a microwave. The reaction mixture was then purified by preparative HPLC using a Sunfire Prep 5 μm C18, 75×30 mm column eluting with a gradient of 05-25% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA) using basic buffer to afford 1-(7-iodo-2H-pyrazolo[4,3-b]pyridin-2-yl)-2-methylpropan-2-ol (170 mg, 0.536 mmol, 43.8% yield). MS [M+H] found 318.

Workup

  1. customThe reaction mixture was then purified by preparative HPLC
  2. washeluting with a gradient of 05-25% acetonitrile (containing 0.035% TFA) in water (containing 0.05% TFA)

Sources & evidence

ORD record
ord-80f633b98e2745c4af2e5b689b72d0e1
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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