2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (S)-tert-butyl 2-(7-bromo-6-fluoro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 1751671Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:27])=[C:4]2[C:24](=[CH:25][CH:26]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N:11][C:7]=1[CH2:6][CH2:5]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1C=CC=CC=1>[Br:1][C:2]1[C:3]([F:27])=[C:4]2[C:24](=[CH:25][CH:26]=1)[C:8]1[NH:9][C:10]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[N:11][C:7]=1[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-tert-butyl 2-(7-bromo-6-fluoro-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (324 mg, 0.74 mmol) in benzene (7 mL) was added DDQ (185 mg, 0.82 mmol) and the mixture was heated to 80° C. After stirring for 16 h, the reaction mixture was cooled to rt and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (45% to 100% EtOAc/hexanes) to afford (S)-tert-butyl 2-(7-bromo-6-fluoro-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate (204 mg, 63%).

Workup

temperaturethe reaction mixture was cooled to rt
concentrationconcentrated under reduced pressure
customThe crude residue was purified by silica column chromatography (45% to 100% EtOAc/hexanes)

Sources & evidence

ORD record: ord-cc36db40f91c412eb24e8b77876712e0
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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