Potassium Carbonate → 1-(3-fluorobenzyl)-5-nitro-1H-indazole

HRID 877105Notes

Reaction equation

HRID 877105 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[C:11]3C=CC=C[C:12]=13)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.ClCCl>[F:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[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)[CH:7]=[N:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 67504869HCID 67504869, compound

Product 1

HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-nitrobenzoindazole (8.16 g, 50 mmol), 3-fluorobenzyl bromide (10.4 g, 55 mmol) and potassium carbonate (13.8 g, 100 mmol) in acetone (200 mL) was refluxed overnight. After reaction cooled to room temperature, the reaction mixture was diluted with dichloromethane (100 mL), filtered through silica gel (about 100 g), and rinsed with 1:1 ethyl acetate:dichloromethane (about 100 mL). The residue after concentration was purified with column chromatography eluting with 0-30% ethyl acetate in dichloromethane to give the title compound as a white crystalline solid (the first fraction, 5.69 g, 42%). LCMS ESI(+) m/z: 272 (M+1).

Workup

  1. temperaturewas refluxed overnight
  2. customAfter reaction
  3. filtrationfiltered through silica gel (about 100 g)
  4. washrinsed with 1:1 ethyl acetate
  5. concentrationThe residue after concentration
  6. customwas purified with column chromatography
  7. washeluting with 0-30% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-c6ca13f4567949cb8bcae927ec11db3b
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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