Toluene → HCID 68006358, compound

HRID 1026595Notes

Reaction equation

C1(C)C=CC=CC=1.Br[C:9]1[CH:34]=[N:33][C:12]2[O:13][C:14]([CH3:32])([CH3:31])[C:15](=[O:30])[N:16]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.[C:53](=O)([O-])[O-:54].[Cs+].[Cs+]>[Cu](I)I.O.CO>[CH3:53][O:54][C:9]1[CH:34]=[N:33][C:12]2[O:13][C:14]([CH3:32])([CH3:31])[C:15](=[O:30])[N:16]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[C:11]=2[CH:10]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a toluene suspension (5.6 ml) of tert-butyl 4-(7-bromo-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (Example 52-1) (1.11 g), copper iodide (24.0 mg), 3,4,7,8-tetramethyl-1,10-phenanthroline (59.6 mg) and cesium carbonate (1.23 g) was added methanol (0.204 ml), followed by stirring at 80° C. for 21 hours. After the reaction solution was brought back to room temperature, water was added, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-methoxy-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (246 mg).

Workup

customwas brought back to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-baffaebab35d4915ac73cd5436e77a75
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729095B2

Reaction notes

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