Cesium carbonate → HCID 67774848, compound

HRID 1802231Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]([CH2:13][CH3:14])[CH3:12])[N:10]=[C:4]2[CH:3]=1.[C:15](=[O:22])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[NH2:16].C(=O)([O-])[O-].[Cs+].[Cs+].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>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>[C:18]([O:17][C:15](=[O:22])[NH:16][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]([CH2:13][CH3:14])[CH3:12])[N:10]=[C:4]2[CH:3]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To an argon purged solution of 7-bromo-N-ethyl-N-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (549 mg, 2.15 mmol) in dioxane (20.6 ml) were added tert-butyl carbamate (303 mg, 2.58 mmol), cesium carbonate (982 mg, 3.01 mmol), tris(dibenzylideneacetone) dipalladium(0) (39.4 mg, 43.0 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (49.8 mg, 86.1 mmol). The resulting mixture was heated to 100° C. and stirred for 2.5 days (weekend) under argon atmosphere. The crude material was applied on silicagel and purified by flash chromatography over a 50 g silicagel column using heptane/ethyl acetate 10-50% as eluent affording [2-(ethyl-methyl-amino)-[1,2,4]triazolo[1,5-a]pyridin-7-yl]-carbamic acid tert-butyl ester (509 mg, 81.2%) as a white solid. mp: 181-183° C., MS: m/z=292.3 (M+H+)

Workup

custompurified by flash chromatography over a 50 g silicagel column

Sources & evidence

ORD record: ord-5c3adaafdf0e49c49890842368d0a6b6
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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