Cesium carbonate → (R)-tert-butyl 3-(1-methyl-3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

HRID 1465705Notes

Reaction equation

HRID 1465705 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([C@@H:16]4[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]4)[N:13]([CH3:29])[N:12]=3)[CH:9]=2)[NH:4][N:3]=1.[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[CH3:29][N:13]1[C:14]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17]2)=[N:15][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)=[N:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178481728HCID 178481728, compound

Product 1

HCID 67517332(R)-tert-butyl 3-(1-methyl-3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylateYield 604.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Stirred a mixture of (R)-tert-butyl 3-(3-(3-bromo-1H-indazol-5-yl)-1-methyl-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate (50 mg, 0.0108 mmol), 4-pyridyl boronic acid (50 mg, 0.409 mmol), PdCl2dppf (10 mg, 0.0136 mmol), cesium carbonate (60 mg, 0.1846 mmol) in dioxane/H2O (v/v 3/1, 4 ml) at 100° C. in a microwave oven for 2 hours. Reaction was cooled, extracted with DCM (50 ml), washed with H2O (20 ml). Dried (Na2SO4), filtered and solvent evaporated to yield (R)-tert-butyl 3-(1-methyl-3-(3-(pyridin-4-yl)-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate as a white solid (30 mg).

Workup

  1. customReaction
  2. temperaturewas cooled
  3. extractionextracted with DCM (50 ml)
  4. washwashed with H2O (20 ml)
  5. dry with materialDried (Na2SO4)
  6. filtrationfiltered
  7. customsolvent evaporated

Sources & evidence

ORD record
ord-4bf5442777fa4af8b5329c1aa6b4e361
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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