Potassium Carbonate → tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate

HRID 1465711Notes

Reaction equation

HRID 1465711 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[N:6]=[C:5]2[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1.[NH:36]1[CH:40]=[CH:39][C:38]([CH:41]2[CH2:46][CH2:45][CH2:44][N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:42]2)=[N:37]1.CN(C)[C@@H]1CCCC[C@H]1N.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.[Cu]I>[N:33]1[CH:34]=[CH:35][C:30]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([N:36]4[CH:40]=[CH:39][C:38]([CH:41]5[CH2:46][CH2:45][CH2:44][N:43]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[CH2:42]5)=[N:37]4)[CH:3]=3)[N:7]([C:11]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:6]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 675181465-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazoleHCID 178451848HCID 178451848, compound

Product 1

HCID 67518079tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylateYield 110.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of 5-iodo-3-(pyridin-4-yl)-1-trityl-1H-indazole (281 mg, 0.5 mmol), tert-butyl 3-(1H-pyrazol-3-yl)piperidine-1-carboxylate (151 mg, 0.6 mmol), copper (I) iodide (19 mg, 0.1 mmol), rac-trans-N,N-dimethylcyclohexane-1,2-diamine (57 mg, 0.4 mmol), K2CO3 (552 mg, 4 mmol) in toluene (3 mL) was heated at 100° C. for 4 days. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, and washed with EtOAc. The filtrate was concentrated and column purified with mixture of methanol, dichloromethane and ammonia to give tert-butyl 3-(1-(3-(pyridin-4-yl)-1-trityl-1H-indazol-5-yl)-1H-pyrazol-3-yl)piperidine-1-carboxylate (380 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a pad of celite
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. customcolumn purified with mixture of methanol, dichloromethane and ammonia

Sources & evidence

ORD record
ord-ddaab4b32d164d4ba61cb8f0088256f9
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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