Bromine → (z)-Methyl 4-(7-bromo-2-oxo-2,3-dihydro-1h-thieno[2,3-e][1,4]diazepin-5-yl)benzoate

HRID 718124Notes

Reaction equation

[O:1]=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[C:5]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[Br:22]Br>N1C=CC=CC=1>[Br:22][C:10]1[S:9][C:7]2[NH:8][C:2](=[O:1])[CH2:3][N:4]=[C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=3)[C:6]=2[CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a 20 mL dram screw-cap vial with septum was dissolved compound 493 (0.140 g, 0.466 mmol) in pyridine (3 mL) to give an orange solution. The mixture was cooled to 0° C. and bromine (0.029 mL, 0.559 mmol) was added dropwise. The reaction mixture was left to stir at 0° C. for 1 hour. The mixture was quenched with saturated thiosulfate solution and extracted with ethyl acetate. The organic layer was washed several times with water, then brine, dried over magnesium sulfate, filtered and evaporated. The residue was suspended in ether and filtered to afford title compound 494 (101 mg, 57%) as a tan solid. MS (m/z): 379.33 (M+H).

Workup

customIn a 20 mL dram screw-cap vial with septum
customto give an orange solution
waitThe reaction mixture was left
customThe mixture was quenched with saturated thiosulfate solution
extractionextracted with ethyl acetate
washThe organic layer was washed several times with water
dry with materialbrine, dried over magnesium sulfate
filtrationfiltered
customevaporated
filtrationfiltered

Sources & evidence

ORD record: ord-7ee981075d764610900ee29067685ea6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193749B2

Reaction notes

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