1,10-Phenanthroline → 6-benzyloxy-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

HRID 1054919Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][N:9]([S:12]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C:10]=2[N:11]=1.N1[C:35]2[C:26](=[CH:27][CH:28]=[C:29]3[C:34]=2N=CC=C3)[CH:25]=CC=1.C([O-])([O-])=[O:37].[Cs+].[Cs+]>C(O)C1C=CC=CC=1.[Cu]I>[CH2:25]([O:37][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][N:9]([S:12]([C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)(=[O:14])=[O:13])[C:10]=2[N:11]=1)[C:26]1[CH:35]=[CH:34][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To 6-bromo-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (50 mg, 140 mmol) in benzyl alcohol (400 μL) was added CuI (15 mg, 79 mmol), 1,10-phenanthroline (15 mg, 83 mmol), and Cs2CO3 (70 mg, 210 mmol). The resulting mixture was heated to 130° C. for 2 hours. Next, the reaction mixture was cooled to room temperature and quenched with a small amount of water, then extracted with ethyl acetate. The aqueous phase was discarded and the organic phase concentrated under reduced pressure. The resulting residue was purified by HPLC to afford 6-benzyloxy-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine. LCMS (ESI): calc. C21H20N2O4S=396; obs. M+H=397.

Workup

temperatureNext, the reaction mixture was cooled to room temperature
customquenched with a small amount of water
extractionextracted with ethyl acetate
concentrationthe organic phase concentrated under reduced pressure
customThe resulting residue was purified by HPLC

Sources & evidence

ORD record: ord-03040abecfbc4ad980662300fa0020db
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394315B2

Reaction notes

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