Potassium Carbonate → HCID 68618801, compound

HRID 1162236Notes

Reaction equation

HRID 1162236 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[O:22][CH:23]=[CH:24][N:25]=1.[NH4+].[Cl-]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]1[O:22][CH:23]=[CH:24][N:25]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 25517Ammonium ChlorideHCID 219575432-(Chloromethyl)-1,3-oxazole

Product 1

HCID 68618801HCID 68618801, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-nitroindazole (500 mg, 3.07 mmol), potassium carbonate (889 mg, 6.44 mmol) and 2-(chloromethyl)-1,3-oxazole (396 mg, 3.37 mmol) in DMF (3 mL) was stirred for 3 hours at room temperature. Saturated NH4Cl was added and the mixture was extracted with dichloromethane. After evaporation, the residue was purified on silica gel (30 to 35% EtOAc/petroleum ether) to give 5-nitro-1-(1,3-oxazol-2-ylmethyl)-1H-indazole (474 mg, 63%); NMR spectrum (CDCl3) 5.76 (s, 2H), 7.11 (s, 1H), 7.60 (d, 1H), 7.62 (s, 1H) 8.26 (s, 1H), 8.31 (d, 1H), 8.74 (s, 1H).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customAfter evaporation
  3. customthe residue was purified on silica gel (30 to 35% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-7f29a256e8f94401a5e70c64198a0a15
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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