Hydrochloric Acid → 4,5-Difluoro-N6-(2-fluoro-4-iodo-phenyl)-benzofuran-6,7-diamine

HRID 1914890Notes

Reaction equation

Cl.[F:2][C:3]1[C:8]2[CH:9]=[CH:10][O:11][C:7]=2[C:6]([N+:12]([O-])=O)=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:4]=1[F:24].C(OCC)(=O)C>C1COCC1.CCCCCC.[Zn]>[F:2][C:3]1[C:8]2[CH:9]=[CH:10][O:11][C:7]=2[C:6]([NH2:12])=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:4]=1[F:24]

Participants

Conditions

Temperature: 30 °C

Procedure

Concentrated HCl (1 mL) was added to a solution of (4,5-difluoro-7-nitro-benzofuran-6-yl)-(2-fluoro-4-iodo-phenyl)-amine (0.260 g, 0.599 mmol) in THF (5 mL) at 0° C. This was followed by the addition of zinc dust (0.179 g, 5.99 mmol) at 0° C. The reaction mass was stirred for 1 hour at 20-40° C. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mass was concentrated under reduced pressure and the concentrate was extracted with ethyl acetate (50 mL). The organic layer was washed with water, brine solution, dried over sodium sulphate and concentrated under reduced pressure to afford 0.240 g of the crude compound which used for the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ 7.53 (d, 1H), 7.49 (dd, 1H), 7.20 (d, 1H), 6.00 (d, 1H), 6.20 (t, 1H), 5.42 (bs, 1H), 4.10 (bs, 2H).

Workup

concentrationThe reaction mass was concentrated under reduced pressure
extractionthe concentrate was extracted with ethyl acetate (50 mL)
washThe organic layer was washed with water, brine solution
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-987b9b1190d0497ba338ce9c63e86de1
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614239B2

Reaction notes

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