Sodium Bicarbonate → 5-(Piperidin-4-YL)-1H-indazole

HRID 1487922Notes

Reaction equation

HRID 1487922 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]3[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(=O)(O)[O-].[Na+]>ClCCl.FC(F)(F)C(O)=O>[NH:13]1[CH2:12][CH2:11][CH:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 49760224tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate2×

Product 1

HCID 497608595-(Piperidin-4-YL)-1H-indazoleYield 82.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of tert-butyl 4-(1H-indazol-5-yl)piperidine-1-carboxylate (compound 62.4, 200 mg, 0.60 mmol) in dichloromethane (3 mL) and trifluoroacetic acid (1 mL). The resulting solution was stirred for 1 h at room temperature, then the pH of the solution was carefully adjusted to 8-9 with aqueous sodium bicarbonate (aq. sat.). The mixture was extracted with dichloromethane (3×30 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compounds as a yellow oil (100 mg, 75%).

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. extractionThe mixture was extracted with dichloromethane (3×30 mL)
  3. dry with materialthe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84fc322b91a34b6ba55bcfc66a1c67dc
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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