Sodium Carbonate → HCID 178498932, compound

HRID 1423914Notes

Reaction equation

HRID 1423914 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.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>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:23]1[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=1)[CH:9]=2)=[O:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 178498916HCID 178498916, compound

Product 1

HCID 178498932HCID 178498932, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 7-bromo-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Example 5e) (180 mg, 0.57 mmol) in dimethoxyethane (DME) (2.5 mL) was added 4-methoxyphenylboronic acid (104 mg, 0.69 mmol), Pd(PPh3)4 solid (66 mg, 0.06 mmol) and then 2M aqueous Na2CO3 solution (0.7 mL). The resulting mixture was purged with nitrogen gas for 1 min and heated to reflux for 2 h. After cooling the reaction mixture was diluted with water (50 mL) and acidified using 1 N HCl to pH 3-4. The precipitate was collected by filtration, rinsed with water and dissolved in CH2Cl2. The organic solution was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was triturated with MeOH (5 mL) and the solid collected, rinsed with MeOH (2 mL) and dried in vacuo to provide 4-hydroxy-7-(4-methoxy-phenyl)-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (139 mg). MS ESI(+) m/e: 343.11 (M+1).

Workup

  1. customThe resulting mixture was purged with nitrogen gas for 1 min
  2. temperatureheated
  3. temperatureto reflux for 2 h
  4. temperatureAfter cooling the reaction mixture
  5. additionwas diluted with water (50 mL)
  6. filtrationThe precipitate was collected by filtration
  7. washrinsed with water
  8. dissolutiondissolved in CH2Cl2
  9. washThe organic solution was washed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude product was triturated with MeOH (5 mL)
  14. customthe solid collected
  15. washrinsed with MeOH (2 mL)
  16. customdried in vacuo

Sources & evidence

ORD record
ord-63a350638b2d4582b03687ff89af5a0e
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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