Cesium carbonate → HCID 67776770, compound

HRID 1802149Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[N:10]=[C:4]2[CH:3]=1.[C:17](=[O:24])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[NH2:18].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>[O:14]1[CH2:15][CH2:16][N:11]([C:9]2[N:10]=[C:4]3[CH:3]=[C:2]([NH:18][C:17](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:7]=[CH:6][N:5]3[N:8]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 110 °C

Procedure

To an argon purged solution of 4-(7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)morpholine (321 mg, 1.13 mmol) in dioxane (8 ml) are added tert-butyl carbamate (159 mg, 1.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (20.8 mg, 22.7 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26.2 mg, 45.4 μmol) and cesium carbonate (517 mg, 1.59 mmol). The reaction vessel is sealed and heated to 110° C. for 20 hours. The crude material is applied on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 10-70% as eluent affording tert-butyl 2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (365 mg, 101%) as a light yellow solid. mp.: 92-3° C. MS: m/z=320.1 (M+H+).

Workup

customThe reaction vessel is sealed
custompurified by flash chromatography on a 20 g silica column

Sources & evidence

ORD record: ord-2393d27c215b47d793a167c03b22b165
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349824B2

Reaction notes

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