Cesium carbonate → HCID 67774330, compound

HRID 1802237Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[N:10]=[C:4]2[CH:3]=1.[C:16](=[O:23])([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[NH2:17].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:19]([O:18][C:16](=[O:23])[NH:17][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[N:10]=[C:4]2[CH:3]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 100 °C

Procedure

To an argon purged solution of 7-bromo-2-(pyrrolidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine (383 g, 1.43 mol) in dioxane (14.4 ml) were added tert-butyl carbamate (202 g, 1.72 mol), cesium carbonate (654 g, 2.01 mol), tris(dibenzylideneacetone) dipalladium(0) (26.3 g, 28.7 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (33.2 g, 57.4 mmol). The resulting mixture was heated to 100° C. and stirred for 18 hours under argon atmosphere. The crude 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-pyrrolidin-1-yl-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-carbamic acid tert-butyl ester (346 mg, 79.5%) as an off-white solid. mp: 216-219° C., MS: m/z=304.1 (M+H+)

Workup

custompurified by flash chromatography over a 20 g silicagel column

Sources & evidence

ORD record: ord-a61f6a9482864e6a8d0df90c2ccf87ae
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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