Sodium Carbonate → HCID 178446749, compound

HRID 384067Notes

Reaction equation

HRID 384067 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([CH3:11])[C:3]=12.[CH3:12][C:13]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=1)([CH2:23][CH3:24])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[CH3:12][C:13]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][N:9]=[C:10]([CH3:11])[C:3]=23)[CH:30]=1)([CH2:23][CH3:24])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67493006HCID 67493006, compoundHCID 178434442HCID 178434442, compound

Product 1

HCID 178446749HCID 178446749, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

4-iodo-3-methyl-1H-pyrazolo[3,4-b]pyridine (150 mg, 0.5790 mmol), tert-butyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (225.4 mg, 0.5790 mmol), Na2CO3 (868.5 μL of 2 M, 1.737 mmol) and Pd(PPh3)4 (66.91 mg, 0.05790 mmol) were placed in a microwave tube and Dioxane (1.500 mL) was added. The resulting suspension was stirred at 150° C. in the microwave (using a 10 minute ramp and nitrogen cooling) for 45 minutes. The reaction mixture was partitioned between EtOAc and brine. The aqueous layer was extracted with EtOAc (3×20 mL) and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow gum. The mixture was purified by column chromatography (75% EtOAc in hexanes, ˜75 mL silica) to give a slightly yellow gum (203 mg, 89% Yield).

Workup

  1. waitramp and nitrogen cooling) for 45 minutes
  2. customThe reaction mixture was partitioned between EtOAc and brine
  3. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow gum
  8. customThe mixture was purified by column chromatography (75% EtOAc in hexanes, ˜75 mL silica)

Sources & evidence

ORD record
ord-e725800c6e7049ecaeb7c0c3c27efbfa
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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