Ethanol → Ethyl 7-sulfamoyl-1-naphthoate

HRID 528795ノート

反応式

HRID 528795 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 71060767Ethyl 7-sulfamoyl-1-naphthoate収率 13%

試薬・触媒・溶媒 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)触媒HCID 167845palladium(II) acetate触媒

反応条件

温度
100 °C

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-6a22f528a39d4d10b123cf0439252f1e
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

反応ノート

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