Pyridine → HCID 12018608, compound

HRID 2301811Notes

Reaction equation

HRID 2301811 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-0550b07f41ed404fac455a14cabb2c70
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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