Water → HCID 57975871, compound

HRID 1865660Notes

Reaction equation

HRID 1865660 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:14]=[C:13](I)[CH:12]=[C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])[CH:5]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[C:33]2[C:28](=[N:29][CH:30]=[C:31](B3OC(C)(C)C(C)(C)O3)[CH:32]=2)[N:27]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[N:26]=1.O>O1CCCC1.C(#N)C>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:14]=[C:13]([C:31]2[CH:32]=[C:33]3[C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][CH3:17])=[N:26][N:27]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:48])([CH3:50])[CH3:49])[C:28]3=[N:29][CH:30]=2)[CH:12]=[C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 57975742HCID 57975742, compoundHCID 598360923-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 57975871HCID 57975871, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

In a personal chemistry microwave vial 5-Iodo-N,N-dimethyl-isophthalamic acid methyl ester (0.75 g, 2.25 mmol), 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine (1.08 g, 2.25 mmol) in tetrahydrofuran/acetonitrile/1 N aqueous sodium carbonate (20 ml) was degassed with nitrogen and 1,1′-bis(diphenylphosphino) ferrocenepalladium(II)-dichloride dichloromethane adduct (0.184 g, 0.23 mmol) was added and the vial sealed. This reaction mixture was irradiated in a microwave vial to 100° C. for 30 minutes. 100 ml water was added and this mixture was extracted with ethyl acetate (3×) the combined organic layers were dried over Magnesium Sulfate and purified by silica gel chromatography to yield 5-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-isophthalamic acid methyl ester as a white solid (0.87 g, 69% yield). MS: m/z 583.7 (M+H+).

Workup

  1. additionwas added
  2. customThis reaction mixture was irradiated in a microwave vial to 100° C. for 30 minutes
  3. extractionthis mixture was extracted with ethyl acetate (3×) the combined organic layers
  4. dry with materialwere dried over Magnesium Sulfate
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-022ce0f1d48546abba4d21d78976b0b0
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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