6-Oxabicyclo[3.1.0]hexane → HCID 90000983, compound

HRID 523060Notes

Reaction equation

HRID 523060 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][CH2:25][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:26]3[CH2:25][CH2:24][CH2:23][CH:27]3[OH:28])[CH:19]=1)=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 10796Cesium carbonateHCID 89995577HCID 89995577, compound

Product 1

HCID 90000983HCID 90000983, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of Cs2CO3 (45.4 mg, 0.139 mmol), 3-chloro-6-(1H-pyrazol-4-yl)isoquinoline (16 mg, 0.070 mmol) and 6-oxabicyclo[3.1.0]hexane (Preparation 37, 23.4 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 (11 mg, 50%).

Workup

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

Sources & evidence

ORD record
ord-0682dd2064294aa0aa634738d16b08a9
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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