Acetonitrile → 5-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole

HRID 624045Notes

Reaction equation

HRID 624045 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Br[CH2:10][CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=2)[NH:14][CH:13]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC#N>O.C(Cl)Cl.CN(C=O)C>[CH3:22][O:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:11][CH2:10][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 111078683-(2-bromoethyl)-5-methoxy-1H-indole

Product 1

HCID 867042135-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A microwave vial was charged with 4-nitro-1H-pyrazole (1.0 g, 8.84 mmol), 3-(2-bromoethyl)-5-methoxy-1H-indole (2.25 g, 8.84 mmol), Cs2CO3 (5.76 g, 17.69 mmol), MeCN (75.0 mL) and DMF (5.0 mL). The tube was sealed and the reaction mixture was irradiated in the microwave to 100° C. for 10 min with cooling. The reaction mixture was diluted with water and DCM, then the org. layer was separated and the aq. layer was extracted with DCM. The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/hex 1:4) to yield 5-methoxy-3-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)-1H-indole as a yellow solid, which was used in the next step without further purification. LC-MS conditions B: tR=0.70 min, [M+H]+=287.13.

Workup

  1. customThe tube was sealed
  2. customthe reaction mixture was irradiated in the microwave to 100° C. for 10 min
  3. temperaturewith cooling
  4. customlayer was separated
  5. extractionthe aq. layer was extracted with DCM
  6. dry with materiallayers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification

Sources & evidence

ORD record
ord-1b0bcc9eb0904ec8847d38eeee658650
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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