3-Pyridinylboronic acid → Carbamic acid, N-[2-(3-pyridinyl)[1,2,4]triazolo[1,5-a]pyridin-7-yl]-, 1,1-dimethylethyl ester

HRID 1802217Notes

Reaction equation

HRID 1802217 reaction equation
Br[C:2]1[N:18]=[C:5]2[CH:6]=[C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]2[N:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:2]2[N:18]=[C:5]3[CH:6]=[C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[CH:9][N:4]3[N:3]=2)[CH:20]=1

Participants

7

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 67774787HCID 67774787, compound

Product 1

HCID 67776082Carbamic acid, N-[2-(3-pyridinyl)[1,2,4]triazolo[1,5-a]pyridin-7-yl]-, 1,1-dimethylethyl esterYield 55.1%

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

Nitrogen is bubbled for 10 minutes through a mixture of tert-butyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (1.39 g, 4.44 mmol) and pyridin-3-ylboronic acid (818 mg, 6.66 mmol) in dioxane (23.8 ml) and sat. aqueous sodium carbonate sol. (5.94 ml), then 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (181 mg, 222 μmol) is added and the resulting mixture is fluxed for 18 hours under nitrogen atmosphere. The residue is diluted with dichloromethane and washed with water; the organic layer is separated, dried with magnesium sulfate and the solvent is removed under reduced pressure. The residue is loaded on silicagel and purified by chromatography on a 50 g silica column using heptane/ethyl acetate 50-100% as eluent affording tert-butyl 2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (762 mg, 55.1%) as a light brown foam. MS: m/z=312.4 (M+H+).

Workup

  1. washwashed with water
  2. customthe organic layer is separated
  3. dry with materialdried with magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. custompurified by chromatography on a 50 g silica column

Sources & evidence

ORD record
ord-95c3fbb451054464b667282756f32af0
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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