Diethyl Ether → 2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamine

HRID 626681Notes

Reaction equation

HRID 626681 reaction equation
C(OC(=O)[NH:7][C:8]1[C:13]2=[CH:14][N:15]([C:17]3[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[N:16]=[C:12]2[CH:11]=[CH:10][N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(OCC)C>C(Cl)Cl>[Cl:24][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([F:23])[C:17]=1[N:15]1[CH:14]=[C:13]2[C:8]([NH2:7])=[N:9][CH:10]=[CH:11][C:12]2=[N:16]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 69671929[2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 696714132-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamineYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-yl]-carbamic acid tert-butyl ester (137 mg) in DCM (1 mL)) at 0° C. was added TFA (1 mL). The reaction mixture was stirred at room temperature for 1 hour then concentrated under reduced pressure. The resultant residue was partitioned between ethyl acetate and sodium bicarbonate (sat. aq.). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give a colourless oil. Trituration with diethyl ether gave the title compound as a white solid (100 mg, 91% yield). LCMS (Method C): RT=0.34 min and 1.79 min, m/z: 263 [M+H+].

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe resultant residue was partitioned between ethyl acetate and sodium bicarbonate (sat. aq.)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a colourless oil

Sources & evidence

ORD record
ord-7d2bfac45dcc4cd49747cea0c0a5f5f3
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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