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

HRID 1627158Notes

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 C8H4FIN2O, 291; found, 291.5.

Workup

filtrationAn orange precipitate was collected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-a73d16bc99b24174b6f9b3f72e5ae241
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785429B2

Reaction notes

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