Cesium carbonate → HCID 89995739, compound

HRID 523059Notes

Reaction equation

HRID 523059 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:18]1[CH:19]=[N:20][NH:21][CH:22]=1)=[CH:13][CH:12]=2.[CH:23]12[O:28][CH:27]1[CH2:26][O:25][CH2:24]2>CN(C=O)C>[Cl:7][C:8]1[N:9]=[CH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:18]1[CH:22]=[N:21][N:20]([CH:27]3[CH2:26][O:25][CH2:24][CH:23]3[OH:28])[CH:19]=1)=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 675113,6-Dioxabicyclo[3.1.0]hexaneHCID 89995577HCID 89995577, compound

Product 1

HCID 89995739HCID 89995739, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Cs2CO3 (34 mg, 0.105 mmol), 3-chloro-6-(1H-pyrazol-4-yl)isoquinoline (16 mg, 0.070 mmol) and 3,6-dioxabicyclo[3.1.0]hexane (Preparation 37, 24 mg, 0.279 mmol) in DMF (3 mL) was stirred at 120° C. under microwave irradiation for 60 minutes. The reaction was cooled, concentrated in vacuo and purified using Biotage silica gel column chromatography eluting with 50-75% EtOAc/cyclohexane to give the title compound as white solid (10 mg, 46%).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. custompurified
  4. washeluting with 50-75% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-ec3ef15916ff4be4a4e1fd7d4d267d69
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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