Tetrahydrofuran → 2-(benzyloxy)-4-(3,4-difluoro-1H-pyrrol-1-yl)aniline

HRID 1528057Notes

Reaction equation

C1COCC1.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([N:23]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24]2)[CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Zn].C(O)(=O)C>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([N:23]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24]2)[CH:17]=[CH:18][C:19]=1[NH2:20])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of zinc (33.7 g), THF (40 mL) and acetic acid (80 mL) was added dropwise a mixture of 1-[3-(benzyloxy)-4-nitrophenyl]-3,4-difluoro-1H-pyrrole (8.52 g), THF (80 mL) and acetic acid (40 mL) at 0° C., and the mixture was stirred at 0° C. for 15 min. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized from hexane/ethyl acetate to give the title compound (7.53 g).

Workup

additionwas added dropwise
filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-fd6d4008a0b54f8199876b4b1ae94bc0
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090586B2

Reaction notes

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