Trifluoroacetic acid → tert-butyl 3-(1-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate

HRID 1465712Notes

Reaction equation

HRID 1465712 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:20]=[CH:19][C:18]([CH:21]5[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]5)=[N:17]4)[CH:14]=3)[N:9](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:8]=2)=[CH:3][CH:2]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N:16]4[CH:20]=[CH:19][C:18]([CH:21]5[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]5)=[N:17]4)[CH:14]=3)[NH:9][N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67518079tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate

Product 1

HCID 67517259tert-butyl 3-(1-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylateYield 135%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate (140 mg, 0.2 mmol) in DCM (5 mL) were added triethylsilane (40 mg, 0.34 mmol) and trifluoroacetic acid (1 mL), the reaction mixture was stirred at room temperature for 3 h. After concentration, crude mixture was column purified with mixture of methanol, dichloromethane and ammonia to give tert-butyl 3-(1-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate (120 mg).

Workup

  1. concentrationAfter concentration, crude mixture
  2. custompurified with mixture of methanol, dichloromethane and ammonia

Sources & evidence

ORD record
ord-c04246308ec44124bb5d3b846c28d52a
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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