Cesium carbonate → HCID 86619142, compound

HRID 2238662Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 100 mg of the t-butyl[(1S)-1-(4-bromophenyl)ethyl]carbamate [106-1], 38 mg of 2-aminopyrazine, 6.8 mg of tris(dibenzylideneacetone)(chloroform)dipalladium (0), 7.7 mg of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 217 mg of cesium carbonate, and 3 mL of 1,4-dioxane, was stirred overnight at 100° C. After cooling the reaction mixture back to room temperature, the insolubles were filtered through celite, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by silica gel chromatography, to obtain 50 mg of t-butyl {(1S)-1-[4-(pyrazin-2-ylamino)phenyl]ethyl}carbamate [106-2] as a pale yellow solid.

Workup

temperatureAfter cooling the reaction mixture back to room temperature
filtrationthe insolubles were filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customthe thus obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-75230751ce534736a46c095c9b3f52ce
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718801B2

Reaction notes

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