Ethyl Acetate → 4,5-Difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one

HRID 1914891Notes

Reaction equation

C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[F:13][C:14]1[C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]([NH2:23])=[C:16]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=2[F:32])[C:15]=1[F:33].C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[F:33][C:15]1[C:16]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=3[F:32])[C:6](=[O:7])[NH:23][C:17]=2[C:18]2[O:22][CH:21]=[CH:20][C:19]=2[C:14]=1[F:13]

Participants

Conditions

Temperature: 30 °C

Procedure

CDI (0.144 g, 0.891 mmol) was added to a solution of 4,5-difluoro-N6-(2-fluoro-4-iodo-phenyl)-benzofuran-6,7-diamine (I-31a: 0.240 g, 0.5940 mmol) in dry DCM (5 mL). The reaction mass was stirred 12-16 hours at 20-40° C. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure and the concentrate was extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford the crude compound. Purification by column chromatography on silica gel (30% ethyl acetate in hexane) afforded 0.180 g of the product (70% yield). 1H NMR (DMSO-d6, 300 MHz): δ 12.15 (bs, 1H), 8.12 (d, 1H), 7.95 (dd, 1H), 7.79 (d, 1H), 7.50 (t, 1H), 7.21 (d, 1H).

Workup

concentrationThe reaction mass was concentrated under reduced pressure
extractionthe concentrate was extracted with ethyl acetate
washThe organic layer was washed with water, brine solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure
customto afford the crude compound
customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-5d64c89500b24608821e72efcd40d09c
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614239B2

Reaction notes

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