Sodium Carbonate → HCID 59009137, compound

HRID 545128Notes

Reaction equation

HRID 545128 reaction equation
Br[C:2]1[S:3][C:4]([S:7][CH2:8][C:9]([NH:11][CH2:12][C@@H:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:14]2)=[O:10])=[CH:5][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+].C[O:35][C:36]([C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)=[O:37]>COCCOC.O.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>[C:36]([C:38]1[CH:43]=[CH:42][C:41]([C:2]2[S:3][C:4]([S:7][CH2:8][C:9]([NH:11][CH2:12][C@@H:13]3[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=4)[CH2:14]3)=[O:10])=[CH:5][CH:6]=2)=[CH:40][CH:39]=1)([OH:37])=[O:35]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 59009243HCID 59009243, compound

Product 1

HCID 59009137HCID 59009137, compoundYield 41.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
130 °C

Procedure

The resultant product (200 mg) of Example 31, tetrakistriphenylphosphinepalladium (25 mg), sodium carbonate (200 mg) and 4-methoxycarbonylphenylboronic acid (105 mg) were dissolved in a mixed solution of ethylene glycol dimethylether (4 mL) and water (250 μL), and the mixture was heated under reflux at 130° C. for 6 hrs. Then, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was evaporated under reduced pressure, and the residue was purified by column chromatography using chloroform as an eluent. The eluent was evaporated and the obtained yellow oil was dissolved in ethanol (2 mL). A 1N aqueous sodium hydroxide solution (50 μL) was added and the mixture was stirred overnight at room temperature. The reaction mixture was adjusted to pH=5 with 1N hydrochloric acid, and the mixture was extracted with chloroform. The extract was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (90 mg) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was evaporated under reduced pressure
  4. customthe residue was purified by column chromatography
  5. customThe eluent was evaporated
  6. dissolutionthe obtained yellow oil was dissolved in ethanol (2 mL)
  7. additionA 1N aqueous sodium hydroxide solution (50 μL) was added
  8. extractionthe mixture was extracted with chloroform
  9. customThe extract was dried
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography
  12. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-789adece9f714d798b16dea0d924335b
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

Loading…