Potassium Carbonate → HCID 86708638, compound

HRID 1430937Notes

Reaction equation

HRID 1430937 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]#[N:14])([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH3:21][C@@H:22]1[CH2:24][O:23]1>CN(C=O)C>[OH:23][C@H:22]([CH3:24])[CH2:21][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:13]#[N:14])=[N:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146261(R)-1,2-EpoxypropaneHCID 225672195-Nitro-1H-indazole-3-carbonitrile

Product 1

HCID 86708638HCID 86708638, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

5-nitro-1H-indazole-3-carbonitrile (600 mg, 3.19 mmol, Example 391E) was taken up in DMF (3 ml), and K2CO3 (580 mg, 4.20 mmol) and (R)-2-methyloxirane (1.85 ml, 26.4 mmol) were added. The reaction mixture was heated at 85° C. for 1 h. The reaction mixture was partitioned between half-saturated aq. NH4Cl solution and EtOAc. The organic layer was washed with half-saturated aq. NaHCO3 solution, then brine, dried over MgSO4, filtered and evaporated to dryness. The crude material was purified by flash column chromatography eluting with 0-50% EtOAc/DCM. (R)-1-(2-hydroxypropyl)-5-nitro-1H-indazole-3-carbonitrile (760 mg) was obtained as a colorless film.

Workup

  1. customThe reaction mixture was partitioned between half-saturated aq. NH4Cl solution and EtOAc
  2. washThe organic layer was washed with half-saturated aq. NaHCO3 solution
  3. dry with materialbrine, dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude material was purified by flash column chromatography
  7. washeluting with 0-50% EtOAc/DCM

Sources & evidence

ORD record
ord-da0f2fcfdf8546adb12bc4999c01c629
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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