Sodium Carbonate → HCID 11518117, compound

HRID 2111826Notes

Reaction equation

HRID 2111826 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][CH:13]=2)[C:10](=[O:28])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](Br)[CH:8]=2)[N:3]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC>[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:14][CH:13]=2)[C:10](=[O:28])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11532621HCID 11532621, compound

Product 1

HCID 11518117HCID 11518117, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-methyl-6-bromo-3-{4-[3-(1-piperidinyl)propoxy]phenyl}-4(3H)-quinazolinone synthesized in Example 34 (100 mg, 0.25 mmol) and phenylboronic acid (40 mg, 0.32 mmol) were dissolved in dimethoxyethane (1 mL), and the atmosphere in the system was replaced by nitrogen. 2M sodium carbonate aqueous solution (0.3 mL) and palladium tetrakis (triphenylphosphine) complex (10 mg, 0.012 mmol) were added, and stirred at 80° C. for 3 hours. Ethyl acetate and distilled water were added to the reaction mixture to perform an ethyl acetate extraction. The organic phase was washed with saturated brine and dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (chloroform/methanol=20/1), and the target substance (61 mg, 61%) was obtained as a colorless solid. 1HNMR (400 MHz,CDCl3,δppm): 1.45 (2H, brs), 1.58-1.63 (4H, m), 2.00-2.04 (2H, m), 2.27 (3H, s), 2.42 (4H, brs), 2.50 (2H, t, J=7.2 Hz), 4.07 (2H, t, J=6.4 Hz), 7.04 (2H, d, J=8.8 Hz), 7.15 (2H, d, J=8.8 Hz), 7.36 (1H, t, J=7.6 Hz), 7.46 (2H, t, J=7.6 Hz), 7.67 (2H, d, J=7.2 Hz), 7.72 (1H, d, J=8.4 Hz), 7.98 (1H, d, J=2.0 Hz), 8.46 (1H, s)

Workup

  1. distillationEthyl acetate and distilled water
  2. additionwere added to the reaction mixture
  3. extractionan ethyl acetate extraction
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe product was purified by silica gel column chromatography (chloroform/methanol=20/1)
  7. customthe target substance (61 mg, 61%) was obtained as a colorless solid

Sources & evidence

ORD record
ord-39855fc779ea413da5daf642eae965e5
Source dataset
uspto-grants-2009_04
Patent number
US07521455B2

Reaction notes

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