Ethanol → Ethyl 7-sulfamoyl-1-naphthoate

HRID 528795노트

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HRID 528795 반응식
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]

참가 물질

7

반응물 4

HCID 702EthanolHCID 312751,4-DioxaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 697221528-Iodonaphthalene-2-sulfonamide2회

생성물 1

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

시약·촉매·용매 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)촉매HCID 167845palladium(II) acetate촉매

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온도
100 °C

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-6a22f528a39d4d10b123cf0439252f1e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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