Dimethylformamide → 6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester

HRID 238633Notes

Reaction equation

HRID 238633 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([OH:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(S([C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH2:37][CH3:38])(=[O:36])=[O:35])=[CH:30][N:29]=1)(=O)=O)C.CN(C)C=O>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH2:37][CH3:38])(=[O:35])=[O:36])=[CH:30][N:29]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:16])[CH:11]=2)[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 132780152,5-Bis(ethylsulfonyl)pyridineHCID 673054496-Bromo-4-hydroxy-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 593266036-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl esterYield 41.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-bromo-4-hydroxy-naphthalene-2-carboxylic acid methyl ester (423 mg, 1.5 mmol), potassium carbonate (414 mg, 3 mmol), 2,5-bis-ethanesulfonyl-pyridine (420 mg, 1.6 mmol) and N,N-dimethylformamide (4 mL) was vigorously stirred and heated at 100° C. overnight under an argon atmosphere, then cooled to room temperature, and diluted with ethyl acetate (10 mL). The resulting mixture was washed with water (10 mL×3). The combined aqueous layers were extracted with ethyl acetate (10 mL). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether) to give 6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester (280 mg, 41%, crude yield) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washThe resulting mixture was washed with water (10 mL×3)
  3. extractionThe combined aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e12345daf48a476eb9c1bdbe77e1553f
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

Loading…