Cesium carbonate → Tert-butyl 4-(5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 1020961Notes

Reaction equation

HRID 1020961 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[CH:11][N:10]([CH3:13])[N:9]=2)=[CH:4][N:3]=1.[C:14]([O:18][C:19]([N:21]1[CH2:26][CH:25]=[C:24](B(O)O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C(Cl)Cl.O>[CH3:13][N:10]1[CH:11]=[N:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]3[CH2:25][CH2:26][N:21]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:20])[CH2:22][CH:23]=3)=[N:3][CH:4]=2)=[N:9]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 21931462(1-(tert-Butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)boronic acidHCID 583719812-chloro-5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridine

Product 1

HCID 58371947Tert-butyl 4-(5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2-chloro-5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridine (3BX) (400 mg, 2.06 mmol); N-Tert-Butoxycarbonyl-1,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (1.4 g, 4.53 mmol); Cesium carbonate (2.3 g, 7.07 mmol) and PdCl2dppf (100 mg) in dioxane/H2O (v/v 10:1, 20 ml) was stirred at 100° C. for 2 hours. The reaction was cooled, diluted with CH2Cl2 (300 ml) and H2O (100 ml), organic layer separated, dried over Na2SO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with EtOAc yielding title product 4BX as a solid (400 mg, 57%) MS (MH, 342).

Workup

  1. temperatureThe reaction was cooled
  2. customseparated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customyielding a residue which
  7. customchromatographed on silica gel eluting with EtOAc yielding title product 4BX as a solid (400 mg, 57%)

Sources & evidence

ORD record
ord-55e2fbac581a449383caccb23e896fe8
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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