Potassium Carbonate → HCID 86727452, compound

HRID 519083Notes

Reaction equation

[CH3:1][C@@H:2]1[C:7](=[O:8])[NH:6][N:5]=[C:4]2[CH2:9][O:10][C:11]3[CH:16]=[CH:15][C:14](B4OC(C)(C)C(C)(C)O4)=[CH:13][C:12]=3[N:3]12.[CH2:26]([C@H:33]1[N:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH:36]=[C:35](OS(C(F)(F)F)(=O)=O)[CH2:34]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH2:26]([C@H:33]1[N:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH:36]=[C:35]([C:14]2[CH:15]=[CH:16][C:11]3[O:10][CH2:9][C:4]4=[N:5][NH:6][C:7](=[O:8])[C@@H:2]([CH3:1])[N:3]4[C:12]=3[CH:13]=2)[CH2:34]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (R)-1-methyl-9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,5-dihydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-2(1H)-one (0.515 g, 1.5 mmol), (R)-tert-butyl 6-benzyl-4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.900 g, 2.13 mmol), Pd(dppf)Cl2—CH2Cl2 complex (0.309 g, 0.375 mmol) and K2CO3 (0.622 g, 4.50 mmol) in 1,4-dioxane (15 mL) and water (5 mL) was heated at 90° C. for 4 h. The reaction was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether) to give (R)-tert-butyl 6-benzyl-4-((R)-1-methyl-2-oxo-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.330 g, 45%).

Workup

temperatureThe reaction was cooled to ambient temperature
customThe solvent was removed in vacuo
customthe residue was purified by column chromatography on silica gel (eluting with 30% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-f6a61a76b9fc418cba342cdd19eaaa53
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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