2,6-Dibromopyridine → 3-(6-Bromopyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775107Notes

Reaction equation

HRID 1775107 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]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:10]3=[CH:11][N:12]=2)[CH:2]=1.[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](Br)[N:30]=1>>[Br:28][C:29]1[N:30]=[C:31]([C:15]2[C:9]3[C:10](=[CH:11][N:12]=[C:7]([C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[CH:8]=3)[N:13]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:14]=2)[CH:32]=[CH:33][CH:34]=1

Participants

3

Reactant 2

HCID 122742,6-DibromopyridineHCID 71253848HCID 71253848, compound

Product 1

HCID 866767023-(6-Bromopyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridineYield 67%

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 2,6-dibromopyridine were reacted. The mixture was purified via silica gel chromatography using a gradient of ethyl acetate in heptane to afford 81 mg (67%) of 3-(6-Bromopyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine. ESI MS m/z 482.2 (M+1).

Workup

  1. customwere reacted
  2. customThe mixture was purified via silica gel chromatography

Sources & evidence

ORD record
ord-56dab2c471984422b4fd87ec1d7e1cc0
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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