Sodium Carbonate → HCID 178446750, compound

HRID 1920853Notes

Reaction equation

HRID 1920853 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2I)[NH:4][N:3]=1.[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>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[C:27]2[CH:26]=[C:25]([C:13]([CH3:12])([CH2:23][CH3:24])[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH:30]=[CH:29][CH:28]=2)[NH:4][N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 67493006HCID 67493006, compoundHCID 178478426HCID 178478426, compound

Product 1

HCID 178446750HCID 178446750, compoundYield 46.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

3-chloro-4-iodo-1H-pyrazolo[3,4-b]pyridine (100 mg, 0.3578 mmol), tert-butyl 2-methyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butylcarbamate (139.3 mg, 0.3578 mmol), Na2CO3 (536.5 μL of 2 M, 1.073 mmol) and Pd(PPh3)4 (41.35 mg, 0.03578 mmol) were placed in a microwave tube and Dioxane (1 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. Reaction mixture 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 dark yellow gum. This material was purified by column chromatography (35% EtOAc in hexanes, loaded in DCM, ˜75 mL silica) to give a slightly yellow gum (68.4 mg, 46% Yield).

Workup

  1. waitramp and nitrogen cooling) for 45 minutes
  2. customReaction mixture
  3. custompartitioned between EtOAc and brine
  4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a dark yellow gum
  9. customThis material was purified by column chromatography (35% EtOAc in hexanes, loaded in DCM, ˜75 mL silica)

Sources & evidence

ORD record
ord-13caa617d88e4275bb7abe9a8aab072f
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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