Cesium carbonate → HCID 67774787, compound

HRID 1802247Notes

Reaction equation

HRID 1802247 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.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.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>[C:15]([O:14][C:12](=[O:19])[NH:13][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([Br:1])[N:11]=[C:5]2[CH:6]=1)([CH3:18])([CH3:17])[CH3:16]

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 76.5%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 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 (6.00 g, 21.7 mmol) in dioxane (222 ml) were added tert-butyl carbamate (3.05 g, 26.0 mmol), cesium carbonate (9.88 g, 30.3 mmol), tris(dibenzylideneacetone) dipalladium(0) (397 mg, 433 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (501 mg, 867 μmol). The resulting mixture was heated to 100° C. and stirred for 18 hours under argon atmosphere. The material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 10-70% as eluent affording (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-carbamic acid tert-butyl ester (5.19 g, 76.5%) as a light yellow solid. MS: m/z=313.0 (M+H+).

Workup

  1. custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record
ord-29fb6237410946da97952206e75f193a
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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