Sodium ethanethiolate → 6-Benzo[b]thiophen-5-yl-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol

HRID 732779ノート

反応式

HRID 732779 の反応式
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=4)[C:11]=3[O:22][C:23]3[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:25][CH:24]=3)[CH:8]=[CH:9][C:2]1=2.C([S-])C.[Na+]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[C:11]([O:22][C:23]4[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]5[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]5)=[CH:36][CH:37]=4)=[C:12]4[C:17](=[CH:18][CH:19]=3)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]4)[CH:8]=[CH:9][C:2]1=2

参加物

4

反応物 2

HCID 4459711Sodium ethanethiolateHCID 59751440HCID 59751440、化合物

生成物 1

HCID 685144076-Benzo[b]thiophen-5-yl-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol収率 58.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

Dissolve the compound of Example 50 (240 mg, 0.48 mmol) in dimethylformamide (DMF, 7 mL), add sodium ethanethiolate (EtSNa, 100 mg, 1.19 mmol). Flush the flask with N2 and then heat the reaction mixture to 150° C. Continue to heat the reaction mixture for 0.5 hours, cool to room temperature. Add water (15 mL), and extract the aqueous layer with CH2Cl2 (3×15 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 0-8% MeOH—NH4OH (10/1, v/v) in CH2Cl2) to give 140 mg of crude 6-benzo[b]thiophen-5-yl-5-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-ol. Purify the impure product by preparative HPLC (Gilson) to give 95 mg of the title compound (55%): mass spectrum (ion spray): m/z=496.3 (M+H−TFA).

後処理

  1. customFlush the flask with N2
  2. temperatureto heat the reaction mixture for 0.5 hours
  3. temperaturecool to room temperature
  4. extractionAdd water (15 mL), and extract the aqueous layer with CH2Cl2 (3×15 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify by flash column chromatography (silica gel, 0-8% MeOH—NH4OH (10/1

出典と根拠

ORDレコード
ord-5584b24dfdc54d1f9fc43d55c84f6050
出典データセット
uspto-grants-2009_09
特許番号
US07585977B2

反応ノート

読み込み中…