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

HRID 732779노트

반응식

HRID 732779 반응식
[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

참가 물질

4

반응물 2

HCID 4459711Sodium ethanethiolateHCID 59751440HCID 59751440, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
150 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5584b24dfdc54d1f9fc43d55c84f6050
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585977B2

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