Toluene → HCID 58447860, compound

HRID 592133Notes

Reaction equation

HRID 592133 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9](B(O)O)=[CH:8][CH:7]=1)[CH3:2].Br[C:17]1[CH:22]=[CH:21][N:20]=[N:19][CH:18]=1.C1(C)C=CC=CC=1.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.C(O)C>[N:19]1[CH:18]=[CH:17][C:22]([C:9]2[CH:10]=[CH:11][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:15])=[CH:7][CH:8]=2)=[CH:21][N:20]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 178889274-BromopyridazineHCID 457900024-Ethoxycarbonylmethylphenylboronic acid

Product 1

HCID 58447860HCID 58447860, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a sealed tube were added 4-(2-ethoxy-2-oxoethyl)phenylboronic acid 37-2 (310 mg, 1.5 mmol), 4-bromopyridazine 37-1 (158 mg, 1 mmol), Pd(PPh3)4 (70 mg, 0.1 mmol), toluene (4 mL), ethanol (1 mL) and 2M Na2CO3 (1.5 mL). The reaction mixture was bubbled with nitrogen for 2 minutes and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated sodium bicarbonate aqueous solution and brine. The organic phase was dried over Na2SO4 and then concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(pyridazin-4-yl)phenyl)acetate 37-3 as pale yellow solid. MS m/z 243.1 (M+1)

Workup

  1. customThe reaction mixture was bubbled with nitrogen for 2 minutes
  2. temperatureAfter cooled down to room temperature
  3. additionthe reaction mixture was diluted with ethyl acetate (50 mL)
  4. washwashed with saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-4fa2c843f58b40d6968e587905c2ed5f
Source dataset
uspto-grants-2016_01
Patent number
US09238646B2

Reaction notes

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