2-Bromoisonicotinamide → 2-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)isonicotinamide

HRID 1775109Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([Sn](C)(C)C)=[N:14][N:13](COCC[Si](C)(C)C)[C:10]3=[CH:11][N:12]=2)[CH:2]=1.Br[C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=1)[C:32]([NH2:34])=[O:33]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([C:29]4[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=4)[C:32]([NH2:34])=[O:33])=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:2]=1

Participants

Reactant 2

HCID 46254072-Bromoisonicotinamide

HCID 71253848HCID 71253848, compound

Product 1

HCID 712540002-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)isonicotinamideYield 21%

Procedure

Following the Stille coupling procedure of Example 299, 5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-3-(trimethylstannyl)-1H-pyrazolo[3,4-c]pyridine and 2-bromoisonicotinamide were reacted. The product was deprotected by the procedure of Example 225 and purified via silica gel chromatography using a gradient of methanol in dichloromethane to afford 10 mg (21%) of 302 over two steps. ESI MS m/z 317.1 (M+1). 1H NMR (400 MHz, DMSO): 14.16 (s, 1H), 9.28 (d, J=12.0 Hz, 2H), 8.96 (s, 1H), 8.94 (d, J=5.1 Hz, 1H), 8.62 (d, J=5.3 Hz, 2H), 8.45 (d, J=8.0 Hz, 1H), 8.40 (s, 1H), 7.80 (d, J=5.1 Hz, 1H), 7.76 (s, 1H), 7.55 (dd, J=8.0, 4.7 Hz, 1H)

Workup

customwere reacted
custompurified via silica gel chromatography

Sources & evidence

ORD record: ord-71a8f22112ac49dbaad37c5a7c9070db
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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