2-Fluoro-4-nitrophenol → 7-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-c]pyridine

HRID 1261329Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[OH:21].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:21][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 259 (420 mg, 2.76 mmol), 2-fluoro-4-nitrophenol (651 mg, 4.14 mmol) and K2CO3 (1.14 g, 8.28 mmol) in Ph2O (15 mL) was heated at 200° C. for 6 hours, cooled to room temperature and partitioned between EtOAc and water. Organic phase was collected, dried and concentrated. The residue was purified by flash column chromatography with gradient elution from hexane to hexane/EtOAc (3:1), to afford the title compound 260 (333 mg, 44% yield) as a yellowish solid. MS (m/z): 274.1(M+H) (found).

Workup

temperaturecooled to room temperature
custompartitioned between EtOAc and water
customOrganic phase was collected
customdried
concentrationconcentrated
customThe residue was purified by flash column chromatography with gradient elution from hexane to hexane/EtOAc (3:1)

Sources & evidence

ORD record: ord-f65c147abf8449b2b84f110c784df99c
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470850B2

Reaction notes

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