Sodium Carbonate → HCID 57969739, compound

HRID 1920856Notes

Reaction equation

HRID 1920856 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.[CH3:34][C:35]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49](B2OC(C)(C)C(C)(C)O2)[CH:48]=1)([CH2:45][CH3:46])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH3:34][C:35]([C:47]1[CH:48]=[CH:49][CH:50]=[C:51]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([C:15]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:9]=[C:10]([C:11]([F:12])([F:14])[F:13])[C:3]=23)[CH:52]=1)([CH2:45][CH3:46])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 579697084-Iodo-3-(trifluoromethyl)-1-(triphenylmethyl)-1H-pyrazolo[3,4-b]pyridineHCID 67493006HCID 67493006, compound

Product 1

HCID 57969739HCID 57969739, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

4-iodo-3-(trifluoromethyl)-1-trityl-1H-pyrazolo[3,4-b]pyridine (135 mg, 0.2431 mmol) and tert-butyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (94.65 mg, 0.2431 mmol) were dissolved in dry Dioxane (1 mL) and Na2CO3 (364.6 μL of 2 M, 0.7293 mmol) was added. The solution was degassed (vacuum/nitrogen cycles×5), Pd[P(tBu)3]2 (12.42 mg, 0.02431 mmol) was added and stirred at 60° C. overnight. The reaction was allowed to cool to RT and partitioned between EtOAc and saturated Na2CO3. The aqueous layer was extracted with further EtOAc (3×10 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a dark purple solid. The resulting solid was purified by column chromatography (15% EtOAc in hexanes, ˜75 mL silica) to give a slightly brown gum (164.7 mg, 98% Yield).

Workup

  1. additionwas added
  2. temperatureto cool to RT
  3. custompartitioned between EtOAc and saturated Na2CO3
  4. extractionThe aqueous layer was extracted with further EtOAc (3×10 mL)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a dark purple solid
  9. customThe resulting solid was purified by column chromatography (15% EtOAc in hexanes, ˜75 mL silica)

Sources & evidence

ORD record
ord-160951fd550b44db9db8e1fe9948e04f
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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