Ethanol → Ethyl 7-sulfamoyl-2-naphthoate

HRID 528799Notes

Reaction equation

HRID 528799 reaction equation
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[CH3:16][CH2:17][OH:18].CN([CH:22]=[O:23])C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[S:12]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][C:2]([C:22]([O:18][CH2:17][CH3:16])=[O:23])=[CH:11]2)=[CH:6][CH:7]=1)(=[O:14])(=[O:13])[NH2:15]

Participants

6

Reactant 3

HCID 702EthanolHCID 6228DimethylformamideHCID 710607367-Iodonaphthalene-2-sulfonamide2×

Product 1

HCID 71060692Ethyl 7-sulfamoyl-2-naphthoateYield 34%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
70 °C

Procedure

To a solution of 7-iodonaphthalene-2-sulfonamide (Intermediate 11, 70 mg, 0.21 mmol) in DMF (2.0 mL) and EtOH (2.0 mL, 34.2 mmol) was added bis(triphenylphosphine)palladium chloride (74 mg, 0.11 mmol). After purging the solution with nitrogen, the reaction flask was evacuated and refilled with CO. The reaction mixture was heated to 70° C. for 3 h. Pd(OAc)2 (47 mg, 0.21 mmol) was then added, and the reaction flask was evacuated and refilled with CO. After stirring under CO overnight at 70° C., the reaction mixture was cooled to room temperature, taken up in a biphasic mixture of EtOAc and water, and filtered. The layers were separated and the aqueous layer was extracted with EtOAc (3×). The combined organic fractions were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (20 mg, 34%) as a white solid. 1H NMR (MeOD) δ 8.82 (s, 1H), 8.63 (d, J=1.3 Hz, 1H), 8.22 (d, J=8.8 Hz, 1H), 8.17-8.12 (m, 2H), 8.02 (dd, J=8.6, 2.0 Hz, 1H), 7.52 (s, 2H), 4.40 (q, J=7.0 Hz, 2H), 1.38 (t, J=7.2 Hz, 3H); MS(ESI−) m/z 278.3 (M−H)−.

Workup

  1. customAfter purging the solution with nitrogen
  2. customthe reaction flask was evacuated
  3. additionrefilled with CO
  4. customthe reaction flask was evacuated
  5. additionrefilled with CO
  6. temperaturethe reaction mixture was cooled to room temperature
  7. additiontaken up in a biphasic mixture of EtOAc and water
  8. filtrationfiltered
  9. customThe layers were separated
  10. extractionthe aqueous layer was extracted with EtOAc (3×)
  11. dry with materialThe combined organic fractions were dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-0d65e8f8b1fb470fb9f28c67960a280d
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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