3-Methylbenzenesulphonyl chloride → 6-bromo-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

HRID 1054915Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][NH:9][C:10]=2[N:11]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][CH:15]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:13]=1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][CH2:8][N:9]([S:18]([C:14]3[CH:13]=[C:12]([CH3:22])[CH:17]=[CH:16][CH:15]=3)(=[O:20])=[O:19])[C:10]=2[N:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Bromo-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine (1.0 g, 4.65 mmol) and m-tolylsulfonyl chloride were dissolved in pyridine (10 mL). The resulting mixture was stirred at 80° C. for one hour. An additional portion of m-tolylsulfonyl chloride (0.98 g, 5.12 mmol) was added and the reaction mixture was stirred at 80° C. for 16 hours. Next, excess solvent was removed under vacuum, and the resulting oil was triturated with water to obtain a tan solid, which was collected by vacuum filtration and washed with water and diethyl ether to give 6-bromo-4-(toluene-3-sulfonyl)-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine. Yield 1.3 g (76%). LCMS (ESI): calc. C14H13BrN2O3S=368, 370; obs. M+H=369, 371.

Workup

stirringthe reaction mixture was stirred at 80° C. for 16 hours
customNext, excess solvent was removed under vacuum
customthe resulting oil was triturated with water
customto obtain a tan solid, which
filtrationwas collected by vacuum filtration
washwashed with water and diethyl ether

Sources & evidence

ORD record: ord-78eb02e8693e4bf49384905320076434
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394315B2

Reaction notes

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