3-(Methoxycarbonyl)benzeneboronic acid → HCID 59244300, compound

HRID 912388Notes

Reaction equation

HRID 912388 reaction equation
Cl[C:2]1[C:3]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[C:4]=2[N:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:7]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[CH3:52][O:53][C:54]([C:56]1[CH:57]=[C:58](B(O)O)[CH:59]=[CH:60][CH:61]=1)=[O:55]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:52][O:53][C:54](=[O:55])[C:56]1[CH:57]=[CH:58][CH:59]=[C:60]([C:2]2[C:3]3[CH2:16][CH2:15][N:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[C:4]=3[N:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:7]=2)[CH:61]=1

Participants

6

Reactant 3

HCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 592450134-Chloro-2-morpholin-4-yl-7-pyridin-3-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 59244300HCID 59244300, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-2-morpholin-4-yl-7-pyridin-3-yl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine (317 mg, 1.00 mmol), palladium acetate (11 mg, 5 mol %), S-Phos (41 mg, 10 mol %) and 3-methoxycarbonylphenylboronic acid (637 mg) were dissolved in dimethylformamide (10 ml). Then, argon substitution was carried out three times under ultrasonic irradiation in reduced pressure. The reaction mixture was stirred at 100° C. for 2 hours, and the reaction mixture was allowed to cool to room temperature, and then poured onto water (100 ml). The reaction mixture was extracted twice with ethyl acetate/tetrahydrofuran (4/1, 100 ml), and the combined organic layers were washed with brine, followed by drying over sodium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0 to 50/1), to obtain a colorless solid (374 mg, 90%).

Workup

  1. customunder ultrasonic irradiation in reduced pressure
  2. temperatureto cool to room temperature
  3. additionpoured onto water (100 ml)
  4. extractionThe reaction mixture was extracted twice with ethyl acetate/tetrahydrofuran (4/1, 100 ml)
  5. washthe combined organic layers were washed with brine
  6. dry with materialby drying over sodium sulfate
  7. filtrationAfter the drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (dichloromethane/methanol=100/0 to 50/1)

Sources & evidence

ORD record
ord-483042320e404c43b087b129f52f34b8
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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