Ethanol → Ethyl 7-sulfamoyl-1-naphthoate

HRID 528795Notes

Reaction equation

HRID 528795 reaction equation
I[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([NH2:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[CH3:16][CH2:17][OH:18].C1CCN2C(=NCCC2)CC1.[O:30]1CCOC[CH2:31]1>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].CC([O-])=O.CC([O-])=O.[Pd+2]>[S:12]([C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[C:31]([O:18][CH2:17][CH3:16])=[O:30])=[CH:7][CH:8]=1)(=[O:14])(=[O:13])[NH2:15]

Participants

7

Reactant 4

HCID 702EthanolHCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 697221528-Iodonaphthalene-2-sulfonamide2×

Product 1

HCID 71060767Ethyl 7-sulfamoyl-1-naphthoateYield 13%

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of 8-iodonaphthalene-2-sulfonamide (Intermediate 7, 200 mg, 0.60 mmol) in dioxane (2.0 mL) in a microwave tube was added EtOH (400 μL, 6.00 mmol), molybdenum hexacarbonyl (81 μL, 0.60 mmol) and Pd(OAc)2 (17 mg, 0.075 mmol). DBU (270 μL, 1.80 mmol) was then added, and the sealed tube was placed in the microwave and heated at 100° C. for 20 min. The reaction mixture was cooled to room temperature and quenched with 10% aq. LiCl solution. The solution was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified using preparative HPLC to give the title compound (22 mg, 13%). 1H NMR (CD3OD) δ 9.54 (d, J=0.9 Hz, 1H), 8.31 (dd, J=7.4, 1.2 Hz, 1H), 8.20 (d, J=8.4 Hz, 1H), 8.13 (d, J=8.8 Hz, 1H), 8.00 (dd, J=8.7, 1.9 Hz, 1H), 7.72 (dd, J=8.2, 7.4 Hz, 1H), 4.50 (q, J=7.0 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H); MS (ESI−) m/z 278.4 (M−H)−.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with 10% aq. LiCl solution
  3. extractionThe solution was extracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-6a22f528a39d4d10b123cf0439252f1e
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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