Trimethylsilyl iodide → HCID 178481765, compound

HRID 241973Notes

Reaction equation

HRID 241973 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:14]=[C:13]3[N:15]([CH3:18])[N:16]=[CH:17][C:12]3=[C:11]([O:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)[CH:10]=2)=[CH:5][CH:4]=1.I[Si](C)(C)C>C(#N)C>[CH3:18][N:15]1[C:13]2=[N:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[N:8][CH:7]=3)=[CH:10][C:11]([O:19][C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=3)=[C:12]2[CH:17]=[N:16]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 462186726-(6-methoxypyridin-3-yl)-1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178481765HCID 178481765, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To 6-(6-methoxypyridin-3-yl)-1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridine 117 (110 mg) in acetonitrile (1 mL) was added iodotrimethylsilane (1 mL). The reaction mixture was heated at 70° C. for 3 h and purified by reverse phase HPLC to afford 119 (35.8 mg). MS (ESI) m/z 397.1 (M+1)+

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-29ec9ee2cb2146c18dbd86627cfe58aa
Source dataset
uspto-grants-2014_02
Patent number
US08653098B2

Reaction notes

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