Iodine → 5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde

HRID 1968254Notes

Reaction equation

[F:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[CH:11]=[O:12].[I:13]I.[I-].[Na+].[OH-].[Na+]>CCO.OS([O-])=O.[Na+]>[F:1][C:2]1[CH:7]=[N:6][C:5]2[NH:8][CH:9]=[C:10]([I:13])[C:4]=2[C:3]=1[CH:11]=[O:12]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-fluoro-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (2.45 g, 14.93 mmol) in EtOH (20 mL) was added iodine (4.55 g, 17.91 mmol), sodium iodide (2.68 g, 17.91 mmol) and aqueous NaOH (1N, 15 mL). The reaction mixture was stirred for 4 h at 25° C. and diluted with aqueous NaHSO3 (0.1N). An orange precipitate was collected by filtration and dried under vacuum to afford the title compound as a yellow solid (6.54 g, 82%). [M+H] calc'd for C8H4F1N2O, 291; found, 291.5.

Workup

filtrationAn orange precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-4e2fb422f9cf464981dd4d9da251d01d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420816B2

Reaction notes

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