Phosphorus tribromide → 8-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide

HRID 572742Notes

Reaction equation

[Br:1]P(Br)Br.[CH3:5][N:6]([CH3:32])[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[C:14]2[C:19](=[C:20]([CH:22](O)[CH3:23])[CH:21]=1)[O:18][C:17]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:16][C:15]2=[O:31])=[O:11]>C(Cl)Cl>[BrH:1].[Br:1][CH:22]([C:20]1[CH:21]=[C:12]([C:10]([NH:9][CH2:8][CH2:7][N:6]([CH3:32])[CH3:5])=[O:11])[CH:13]=[C:14]2[C:19]=1[O:18][C:17]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[CH:16][C:15]2=[O:31])[CH3:23]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tribromophosphine 1M in DCM (0.154 mL, 0.15 mmol) at 25° C., was added dropwise to N-(2-(dimethylamino)ethyl)-8-(1-hydroxyethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide (60 mg, 0.15 mmol) suspended in DCM (1 mL). This suspension was stirred at 25° C. for 4 days. The resulting precipitate was collected by filtration, washed with diethyl ether and dried to afford 8-(1-bromoethyl)-N-(2-(dimethylamino)ethyl)-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (98 mg, >100%) as a white solid, which was used without further purification. Mass Spectrum: M+H+ 454.

Workup

filtrationThe resulting precipitate was collected by filtration
washwashed with diethyl ether
customdried

Sources & evidence

ORD record: ord-9391e57ac2f44c37ab95f84da2f063f4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029374B2

Reaction notes

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