Sodium Iodide → 1-Acetyl-5-fluoro-4-iodo-7-azaindole

HRID 1821231Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:10]=[CH:11][C:3]=12.[I-:22].[Na+].[C:24](Cl)(=[O:26])[CH3:25]>C(#N)C>[C:24]([N:9]1[C:4]2=[N:5][CH:6]=[C:7]([F:8])[C:2]([I:22])=[C:3]2[CH:11]=[CH:10]1)(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vial was charged with 4-chloro-5-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine (3.06 mmol, prepared as described in Tetrahedron Lett. 2004, 45, 2317-2319), sodium iodide (4.90 mmol), acetyl chloride (6.43 mmol) and dry acetonitrile (8 mL). The reaction tube was sealed, and heated in a microwave reactor at 150° C. for 15 minutes. Upon cooling to room temperature, the resultant precipitate was collected by filtration and washed with a minimal amount of cold acetonitrile. Drying under high vacuum provided the title compound as a yellow powder which was used without further purification. ESMS [M+H]+: 305.2

Workup

customThe reaction tube was sealed
temperatureUpon cooling to room temperature
filtrationthe resultant precipitate was collected by filtration
washwashed with a minimal amount of cold acetonitrile
customDrying under high vacuum

Sources & evidence

ORD record: ord-e79a07ec97744cd4b17a591f151c55ff
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605266B2

Reaction notes

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