Sodium Carbonate → HCID 178439037, compound

HRID 713175Notes

Reaction equation

HRID 713175 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:17]1[NH:22][C:21](=[N:23][C:24]2[C:29]([CH:30]([CH3:32])[CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[CH:33]([CH3:35])[CH3:34])[CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.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>[C:1]1([C:17]2[NH:22][C:21](=[N:23][C:24]3[C:29]([CH:30]([CH3:31])[CH3:32])=[CH:28][CH:27]=[CH:26][C:25]=3[CH:33]([CH3:35])[CH3:34])[CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 178439035HCID 178439035, compound

Product 1

HCID 178439037HCID 178439037, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

Phenylboronic acid (316 mmol) and Na2CO3 (792 mmol) are dissolved into 200 mL of degassed 1:1 H2O/ethanol. This solution is added to a toluene solution (500 mL) of 6-bromo-2-(2,6-diisopropylphenyl)iminopyridine (109 g, 316 mmol). Inside of a dry box 1 g (0.86 mmol) of tetrakis(triphenylphosphine)palladium(0) is dissolved in 50 mL of degassed toluene. The solution is removed from the dry box and charged into the N2 purged reactor. The biphasic solution is vigorously stirred and heated to 70° C. for 4-12 h. After cooling to room temperature, the organic phase is separated, the aqueous layer is washed with toluene (3×75 mL), and the combined organic extracts are washed with H2O (3×200 mL) and dried over MgSO4. After removing the volatiles under reduced pressure, the resultant light yellow oil is purified via recrystallization from methanol to give a yellow solid. Yield is 109 g, 87.2 percent; mp 142-144° C.

Workup

  1. customof degassed 1:1 H2O/ethanol
  2. customThe solution is removed from the dry box
  3. additioncharged into the N2 purged reactor
  4. temperatureAfter cooling to room temperature
  5. customthe organic phase is separated
  6. washthe aqueous layer is washed with toluene (3×75 mL)
  7. washthe combined organic extracts are washed with H2O (3×200 mL)
  8. dry with materialdried over MgSO4
  9. customAfter removing the volatiles under reduced pressure
  10. customthe resultant light yellow oil is purified via recrystallization from methanol
  11. customto give a yellow solid

Sources & evidence

ORD record
ord-1aff6f31fe1c47489ba05306a45e8db7
Source dataset
uspto-grants-2015_11
Patent number
US09181368B2

Reaction notes

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