Ethanol → HCID 16051642, compound

HRID 2407254Notes

Reaction equation

HRID 2407254 reaction equation
B(O)(O)[C:2]1[CH:7]=[CH:6][C:5]2[O:8][CH2:9][O:10][C:4]=2[CH:3]=1.Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>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.C1(C)C=CC=CC=1>[O:8]1[C:5]2[CH:6]=[CH:7][C:2]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)=[CH:3][C:4]=2[O:10][CH2:9]1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acid2×

Product 1

HCID 16051642HCID 16051642, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-(methylenedioxy)phenylboronic acid (500 mg, 3.0 mmol), 3-bromopyridine (290 μl, 476 mg, 3.0 mmol), 2 M Na2CO3 (3.05 ml, 6.0 mmol), tetrakis(triphenylphosphine)palladium (35 mg, 0.03 mmol), EtOH (0.75 ml) and toluene (3 ml) was heated in a microwave reactor at 120° C. for 40 min. Another crop of 3,4-(methylenedioxy)phenylboronic acid (250 mg, 1.5 mmol) was added and the mixture heated under microwaves at 120° C. for 10 min. The reaction mixture was filtered and the layers were separated. The organic phase was extracted twice with 1 M HCl. All the aqueous phases were combined, basified with 5 M NaOH and extracted twice with EtOAc. The combined organic phases were dried (Na2SO4), filtered and evaporated to give 585 mg of the title compound.

Workup

  1. temperaturethe mixture heated under microwaves at 120° C. for 10 min
  2. filtrationThe reaction mixture was filtered
  3. customthe layers were separated
  4. extractionThe organic phase was extracted twice with 1 M HCl
  5. extractionextracted twice with EtOAc
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-d45eb139eb074e599c3d6e1d716a8873
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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