Cesium carbonate → HCID 67775938, compound

HRID 1802203Notes

Reaction equation

HRID 1802203 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1.[C:14](=[O:21])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH2:15].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH3:12][N:11]([CH3:13])[C:9]1[N:10]=[C:4]2[CH:3]=[C:2]([NH:15][C:14](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:7]=[CH:6][N:5]2[N:8]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 67775541HCID 67775541, compound

Product 1

HCID 67775938HCID 67775938, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To an argon purged solution of 7-bromo-N,N-dimethyl-[1,2,4]triazolo[1,5-a]pyridine-2-amine (300 mg, 1.24 mmol) in dioxane (11 ml) are added tert-butyl carbamate (175 mg, 1.49 mmol), cesium carbonate (568 mg, 1.74 mmol), tris(dibenzylideneacetone)dipalladium(0) (22.8 mg, 24.9 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (28.8 mg, 49.8 μmol). The resulting mixture is stirred for 18 hours at 100° C. under argon atmosphere. The crude material is loaded on silicagel and purified by chromatography on a 20 g silica column using heptane/ethyl acetate 10-70% as eluent affording tert-butyl 2-(dimethylamino)-[1,2,4]triazolo[1,5-a]pyridine-7-ylcarbamate (310 mg, 89.8%) as a yellow foam. MS: m/z=278.3 (M+H+).

Workup

  1. custompurified by chromatography on a 20 g silica column

Sources & evidence

ORD record
ord-1ff8dee62ddd4c939795152bfb7b2e4e
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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