N-methyl-2-pyrrolidone → 7-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamine

HRID 626736Notes

Reaction equation

HRID 626736 reaction equation
Br[C:2]1[C:7]2=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=[C:6]2[C:5]([Br:19])=[CH:4][N:3]=1.C[N:21]1C(=O)CCC1>N>[Br:19][C:5]1[C:6]2[C:7](=[CH:8][N:9]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])[N:10]=2)[C:2]([NH2:21])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 866970594,7-Dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

Product 1

HCID 696714737-Bromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamineYield 84%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A solution of 4,7-dibromo-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (730 mg, 1.73 mmol) in NMP (6.5 mL) and 33% aqueous ammonia (3.5 mL) was sealed in a microwave vial and irradiated in a microwave reactor at 160° C. for 2 hours. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was triturated with ether to afford the title compound as a beige solid (515 mg, 84% yield). LCMS (Method C): RT=2.00 min, m/z: 357 [M+H+].

Workup

  1. customirradiated in a microwave reactor at 160° C. for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-e94b00765d1b4ce58e573c40a1ce301f
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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