Cesium carbonate → HCID 67774787, compound

HRID 1802216Notes

Reaction equation

HRID 1802216 reaction equation
[Br:1][C:2]1[N:11]=[C:5]2[CH:6]=[C:7](Br)[CH:8]=[CH:9][N:4]2[N:3]=1.[C:12](=[O:19])([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[NH2:13].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>[Br:1][C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([NH:13][C:12](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=[CH:9][N:4]2[N:3]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 677742742,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 67774787HCID 67774787, compoundYield 64.7%

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 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1.9 g, 6.86 mmol) in dioxane (70.3 ml) are added tert-butyl carbamate (965 mg, 8.23 mmol), cesium carbonate (3.13 g, 9.61 mmol), tris(dibenzylideneacetone)dipalladium(0) (126 mg, 137 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (159 mg, 274 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 70 g silica column using heptane/ethyl acetate 10-40% as eluent affording tert-butyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (1.39 g, 64.6%) as a white solid. MS: m/z=313.0; 314.9 (M+H+).

Workup

  1. custompurified by chromatography on a 70 g silica column

Sources & evidence

ORD record
ord-fe20415eda154b6eb64d1f9d361fde28
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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