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Sodium Carbonate → 4-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 451481
Notes
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Reaction equation

HRID 451481 reaction equation
Br[C:2]1[C:3]2[N:4]([N:9]=[C:10]([NH2:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.CC1(C)C(C)(C)OB([C:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[NH2:12][C:10]1[N:11]=[C:3]2[C:2]([C:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=3)=[CH:7][C:6]([CH3:8])=[CH:5][N:4]2[N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 214643388-Bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 673361314-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 3

HCID 53485975
CID 53485975
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 8-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.14 g, 5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.39 g, 7.5 mmol), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (204 mg, 250 μmol) and an aqueous solution of Na2CO3 (2 N, 12.5 mL, 25 mmol) in dioxane (50 mL) was stirred at 110° C. over night. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, the solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography using EtOAc as eluent. The title compound was obtained after stirring with diethyl ether, filtration and drying as a light yellow crystalline solid (1.54 g, 93%).

Workup

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-77f426a3870f43ada43768e0dde0d823
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08486967B2

Reaction notes

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