Water → HCID 67492607, compound

HRID 1920862Notes

Reaction equation

HRID 1920862 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:9]=[C:10](B3OC(C)(C)C(C)(C)O3)[CH:11]=2)[CH2:5][CH2:4]1)#[N:2].I[C:33]1[CH:38]=[CH:37][N:36]=[C:35]2[N:39]([C:46]([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)([C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[N:40]=[C:41]([C:42]([F:45])([F:44])[F:43])[C:34]=12.C(=O)([O-])[O-].[Na+].[Na+].O>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.C(OCC)(=O)C>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH:9]=[C:10]([C:33]3[CH:38]=[CH:37][N:36]=[C:35]4[N:39]([C:46]([C:47]5[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=5)([C:53]5[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=5)[C:59]5[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=5)[N:40]=[C:41]([C:42]([F:44])([F:45])[F:43])[C:34]=34)[CH:11]=2)[CH2:4][CH2:5]1)#[N:2]

Participants

8

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 579697084-Iodo-3-(trifluoromethyl)-1-(triphenylmethyl)-1H-pyrazolo[3,4-b]pyridineHCID 57969718HCID 57969718, compound

Product 1

HCID 67492607HCID 67492607, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl N-[3-[3-(1-cyanocyclopropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propyl]carbamate (50 mg, 0.1173 mmol) was dissolved in dioxane (2 mL) and 4-iodo-3-(trifluoromethyl)-1-trityl-pyrazolo[5,4-b]pyridine (65.14 mg, 0.1173 mmol) was added followed by sodium carbonate (176.0 μL of 2 M, 0.3519 mmol). The reaction mixture was degassed and filled with nitrogen 5 times then Pd[P(tBu)3]2 (8.994 mg, 0.01760 mmol) was added and the reaction heated at 60° C. overnight. After cooling, water was added and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate, the combined organics were washed with brine, dried over MgSO4, filtered and the solvent removed under reduced pressure. The crude product was purified on silica (Companion, 12 g) eluting with 2.5-50% EtOAc:Petrol ether to give tert-butyl 3-(3-(1-cyanocyclopropyl)-5-(3-(trifluoromethyl)-1-trityl-1H-pyrazolo[3,4-b]pyridin-4-yl)phenyl)propylcarbamate as a viscous oil (72 mg, 84%).

Workup

  1. customThe reaction mixture was degassed
  2. additionfilled with nitrogen 5 times
  3. temperatureAfter cooling
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe crude product was purified on silica (Companion, 12 g)
  10. washeluting with 2.5-50% EtOAc

Sources & evidence

ORD record
ord-2c8363b5335f4c77bfd787854b25a046
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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