Pyridine → HCID 12018608, compound

HRID 842363Notes

Reaction equation

HRID 842363 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].N1C=CC=CC=1.[N+:24]([C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](Cl)=[O:30])([O-:26])=[O:25]>ClCCl>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=3[N+:24]([O-:26])=[O:25])[CH:15]=2)[CH:10]=[N:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 118752-Nitrobenzoyl chlorideHCID 120186071-BOC-6-AMINO-INDAZOLE

Product 1

HCID 12018608HCID 12018608, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-Boc-6-aminoindazole (1.5 g, 6.4 mmol) in dichloromethane (25 mL) was added pyridine (1.55 mL, 19.2 mmol) followed by 2-nitrobenzoyl chloride (1 mL, 7.1 mmol). After stirring for 12 h, the solvent was removed by rotary evaporation and the residue was partitioned between ethyl acetate (250 mL) and water (250 mL). The aqueous phase was separated and the organic phase was washed with 1 M citric acid, brine, satd aq NaHCO3, and brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo to give 2.64 g of off-white solid.

Workup

  1. customthe solvent was removed by rotary evaporation
  2. customthe residue was partitioned between ethyl acetate (250 mL) and water (250 mL)
  3. customThe aqueous phase was separated
  4. washthe organic phase was washed with 1 M citric acid, brine
  5. dry with materialThe organic phase was then dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29a9f2c8aa0445819bf14fae45e42216
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

Loading…