Methyl iodide → 8-Bromo-2-fluoro-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229317Notes

Reaction equation

[Br:1][C:2]1[CH:20]=[N:19][C:5]2[N:6]([CH2:17][CH3:18])[C:7]3[N:15]=[C:14]([F:16])[CH:13]=[CH:12][C:8]=3[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[Br:1][C:2]1[CH:20]=[N:19][C:5]2[N:6]([CH2:17][CH3:18])[C:7]3[N:15]=[C:14]([F:16])[CH:13]=[CH:12][C:8]=3[N:9]([CH3:23])[C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the 8-bromo-5,11-dihydro-11-ethyl-2-fluoro-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (44 g, 130.5 mmol) in DMF (520 mL) was added NaH (4.28 g, 178 mmol), and the mixture was heated to 50° C. for 30 min. The reaction mixture was cooled to room temperature and treated with MeI (24.4 mL, 522 mmol). After 1.5 h, the reaction mixture was poured over ice water. The solid was filtered, washed with water and then hexane, dried under reduced pressure to give the title compound (43.2 g, 94% yield) as dark grey solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationThe solid was filtered
washwashed with water
dry with materialhexane, dried under reduced pressure

Sources & evidence

ORD record: ord-ee3ec5fd4ef64343ba3d6e26e0bdaf59
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06420359B1

Reaction notes

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