Sodium Carbonate → HCID 58587702, compound

HRID 2251099Notes

Reaction equation

HRID 2251099 reaction equation
Cl[C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:3]3[C:8]([N:9]=[C:10]4[C:15]=2[CH2:14][CH2:13][CH2:12][CH2:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21495Acridine, 1,2,3,4-tetrahydro-9-chloro-HCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 58587702HCID 58587702, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 9-chloro-1,2,3,4-tetrahydro-acridine (282 mg, 1.30 mmol), 4-Benzyloxyphenyl boronic acid (443 mg, 1.94 mmol), tetrakistriphenylphosphine palladium (15 mg, 0.01 mmol), and 2 M aq Na2CO3 (0.97 mL, 1.94 mmol) was heated to 80° C. in 1,2-dimethoxyethane (2 mL) with vigorous stirring overnight in a sealed vial. The reaction mixture was cooled to room temperature and partitioned between EtOAc (50 mL) and H2O (10 mL). The aq. layer was extracted with EtOAc (25 mL). The combined organic layers were washed with sat. aq. NaCl (25 mL), dried over Na2SO4, filtered, and concentrated. The residue was triturated with hexanes (50 mL) and to give a mixture of the desired product and starting chloride, which was used without further purification.

Workup

  1. custompartitioned between EtOAc (50 mL) and H2O (10 mL)
  2. extractionThe aq. layer was extracted with EtOAc (25 mL)
  3. washThe combined organic layers were washed with sat. aq. NaCl (25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with hexanes (50 mL)
  8. customto give

Sources & evidence

ORD record
ord-c2c4e38f6f84433db9a4cc4166f7b2d8
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

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