Sodium Carbonate → (4-{[3-(8-Chloro-3-phenylcinnolin-4-yl)phenoxy]methyl}phenyl)acetic acid

HRID 643299Notes

Reaction equation

HRID 643299 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:7]2[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.Br[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[I].[K]>CN(C=O)C.C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[N:9][C:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[C:7]2[C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=1)[O:24][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 45190564-(Bromomethyl)phenylacetic acidHCID 118564393-(8-Chloro-3-phenylcinnolin-4-yl)phenolHCID 178506587HCID 178506587, compound

Product 1

HCID 11856438(4-{[3-(8-Chloro-3-phenylcinnolin-4-yl)phenoxy]methyl}phenyl)acetic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(8-chloro-3-phenylcinnolin-4-yl)phenol (0.05 g, 0.15 mmol), 4-bromomethylphenyl acetic acid (0.10 g, 0.44 mmol), sodium carbonate (0.50 g, 4.7 mmol), and potassium iodine (0.50 g, 3.0 mmol) in DMF (5 mL)/water (1 mL) was heated to 40° C. for 2 hours. The mixture was then poured into water, acidified with acetic acid and extracted with ethyl acetate. The organic residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a colored solid. MS (ESI) m/z 481; HRMS (ESI, [M+H]+) 481.1329.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min)
  3. customThe product was collected
  4. custombased on UV absorption
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fe501afd24e64b62845eaf9f659f0c93
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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