Sodium Chloride → HCID 22340402, compound

HRID 585315Notes

Reaction equation

HRID 585315 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:17]=3)[CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>C(COC)OC.O1CCCC1.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>[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[C:16]([CH2:21][N:22]([CH3:24])[CH3:23])[CH:17]=4)[CH:12]=3)=[O:10])=[CH:4][CH:3]=2)=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 22340371HCID 22340371, compound

Product 1

HCID 22340402HCID 22340402, compoundYield 30.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(4-Bromophenyl)-6-[(dimethylamino)methyl]-2-naphthamide (128 mg, 0.334 mmol) obtained in Example 4, 4-chlorophenylboronic acid (62.7 mg, 401 mmol) and a 2N aqueous sodium carbonate solution (0.668 ml, 1.34 mmol) were dissolved in a mixed solution of dimethoxyethane (3 ml) and tetrahydrofuran (0.3 ml), tetrakistriphenylphosphinepalladium (11.6 mg, 0.01 mol) was added thereto under the nitrogen atmosphere, and the mixture was stirred at 90° C. for 4 hours. To the reaction solution was added an aqueous saturated sodium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by alumina column chromatography (developing solvent: ethyl acetate), and the insolubles were crystallized from a mixed solution of ethyl acetate and diisopropyl ether (1:3) to obtain the titled compound (42 mg) as a white powder.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by alumina column chromatography (developing solvent: ethyl acetate)
  6. customthe insolubles were crystallized from a mixed solution of ethyl acetate and diisopropyl ether (1:3)

Sources & evidence

ORD record
ord-b4f35f31694941b98cf4c3560052b670
Source dataset
uspto-grants-2005_08
Patent number
US06930185B2

Reaction notes

Loading…