Sodium Carbonate → HCID 57969686, compound

HRID 384084Notes

Reaction equation

HRID 384084 reaction equation
B([O-])[O-].[CH3:4][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=1)([CH3:8])[C:6]#[N:7].[I-].I[C:26]1[C:31]([CH3:32])=[CH:30][N:29]=[C:28]2[NH:33][N:34]=[CH:35][C:27]=12.C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1>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.CC#N.O>[CH3:8][C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:26]2[C:31]([CH3:32])=[CH:30][N:29]=[C:28]3[NH:33][N:34]=[CH:35][C:27]=23)[CH:10]=1)([CH3:4])[C:6]#[N:7]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 86636476HCID 86636476, compoundHCID 178448793HCID 178448793, compound

Product 1

HCID 57969686HCID 57969686, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
150 °C

Procedure

Boronate-2-methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanenitrile (200 mg, 0.7376 mmol), iodide-4-iodo-5-methyl-1H-pyrazolo[3,4-b]pyridine (191.1 mg, 0.7376 mmol), Na2CO3 (1.106 mL of 2 M, 2.213 mmol) and Pd(PPh3)4 (85.23 mg, 0.07376 mmol) were placed in a microwave tube and dry Dioxane (5.000 mL) was added. The resulting suspension was stirred at 150° C. in the microwave (using a 10 minute ramp and nitrogen cooling) for 60 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 an oil. The mixture was purified by column chromatography (10-100% EtOAc in hexanes, ˜100 mL silica, loaded in DCM) to give an oil which was lyophilised from MeCN/H2O to give a solid (217 mg, 57% Yield).

Workup

  1. waitramp and nitrogen cooling) for 60 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 an oil
  8. customThe mixture was purified by column chromatography (10-100% EtOAc in hexanes, ˜100 mL silica, loaded in DCM)
  9. customto give an oil which

Sources & evidence

ORD record
ord-e7590afbcf064b279be0c8508ae2da9c
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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