Phosphorus tribromide → 8-(1-bromoethyl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide hydrobromide

HRID 1187248Notes

Reaction equation

[Br:1]P(Br)Br.O[CH:6]([C:8]1[CH:9]=[C:10]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][C@H:20]([CH3:24])[CH2:19]1)=[CH:14][C:13]2=[O:25])[CH3:7]>ClCCCl.C(OCC)C>[BrH:1].[Br:1][CH:6]([C:8]1[CH:9]=[C:10]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][C@H:20]([CH3:24])[CH2:19]1)=[CH:14][C:13]2=[O:25])[CH3:7]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of tribromophosphine (0.215 mL, 2.29 mmol) in 1,2-dichloroethane (1 mL) at 10° C. was added dropwise to 8-(1-hydroxyethyl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide (750 mg, 2.08 mmol) suspended in 1,2-dichloroethane (9 mL) under nitrogen. The resulting suspension was stirred at 50° C. for 1 hour. The reaction mixture was allowed to cool to RT under stirring and diluted with diethyl ether (40 mL). The precipitate was collected by filtration, washed with diethyl ether and dried to a constant weight to afford 8-(1-bromoethyl)-N,N-dimethyl-2-((R)-2-methylmorpholino)-4-oxo-4H-chromene-6-carboxamide hydrobromide (1.3 g, 124%) as a white solid, which was used without further purification. Mass Spectrum: M+H+ 424.

Workup

temperatureto cool to RT
stirringunder stirring
filtrationThe precipitate was collected by filtration
washwashed with diethyl ether
customdried to a constant weight

Sources & evidence

ORD record: ord-cbc883fd776b4b468ee61fee0b943a90
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673906B2

Reaction notes

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