2-Fluoro-4-iodopyridine-3-carbaldehyde → 1-(3-bromopyridin-2-yl)-4-iodo-1H-pyrazolo[3,4-b]pyridine

HRID 1186812Notes

Reaction equation

F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[Br:11][C:12]1[C:13]([NH:18][NH2:19])=[N:14][CH:15]=[CH:16][CH:17]=1>CN1C(=O)CCC1>[Br:11][C:12]1[C:13]([N:18]2[C:2]3=[N:9][CH:8]=[CH:7][C:6]([I:10])=[C:3]3[CH:4]=[N:19]2)=[N:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 185 °C

Procedure

To a dry 15 mL ChemGlass pressure bottle under N2 was added 2-fluoro-4-iodonicotinaldehyde (725 mg, 2.89 mmol), 3-bromo-2-hydrazinylpyridine (543 mg, 2.89 mmol) and anhydrous NMP (Volume: 4.0 mL). The reaction mixture was flushed with argon, securely capped, and heated to 185° C. for 45 min. The reaction mixture was worked up according to the procedure described in Intermediate 69A and the crude product was purified by Biotage Silica gel chromatography using a 12 g Thompson Single Step™ silica cartridge with a linear gradient from 100% CH2Cl2 to 100% ethyl acetate over 11 column volumes to give 867.4 mg (74.9%) of the title compound as a yellow solid. 1H NMR (500 MHz, CCl3D) δ ppm 8.64 (1 H, dd, J=4.58, 1.53 Hz), 8.09-8.25 (3 H, m), 7.65 (1 H, d, J=4.58 Hz), 7.37 (1 H, dd, J=7.93, 4.58 Hz). LC/MS (Condition B): ret. T=3.2 min, (M+H)+ 400.81, 402.81.

Workup

customThe reaction mixture was flushed with argon
customsecurely capped
customthe crude product was purified by Biotage Silica gel chromatography

Sources & evidence

ORD record: ord-6dbd512d575d46bd9420dfdda518c0ac
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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