Methanol → 6-Methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-(1-pyrrolidinylmethyl)phenyl Ketone

HRID 1387112ノート

反応式

HRID 1387112 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][C:19]=3[S:20][C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:24][CH:23]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[CH:41](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C.CO>CO.CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][C:19]=3[S:20][C:21]=2[C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[CH:26][CH:27]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14]1

参加物

6

反応物 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 167693Trimethylsilyldiazomethane3 回HCID 10650441HCID 10650441、化合物

生成物 1

HCID 211826496-Methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-(1-pyrrolidinylmethyl)phenyl Ketone収率 43.6%

試薬・触媒・溶媒 1

HCID 21959252Acetonitrile methanol溶媒

実験手順

To a mixture of (210 mg, 0.37 mmol) of 6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-methoxy-4-(1-pyrrolidinylmethyl)phenyl ketone (Example 163, Part C) in 2.0 mL of MeOH/CH3CN solution (1:9 ratio) was added (0.091 mL, 0.52 mmol) of diisopropylethylamine and (0.26 mL, 0.52 mmol) 2 M (trimethylsilyl)diazomethane in hexanes at room temperature. The reaction was stirred for 24 h. Another portion (0.20 mL, 0.40 mmol) of 2 M (trimethylsilyl)diazomethane in hexanes was added along with 0.5 mL of MeOH, and the solution was stirred at room temperature for 24 h. Another portion (0.10 mL, 0.20 mmol) of 2 M (trimethylsilyl)diazomethane in hexanes was added, and the solution was stirred at room temperature for 24 h. The reaction mixture was concentrated to dryness under reduced pressure and then taken up in 30 mL of H2O and washed with 25 mL of H2O and 1:1 satd. NaHCO3-brine solution which were back extracted with CH2Cl2 (3×30 mL) and EtOAc (1×30 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash chromatography (silica gel, 7% [10% conc NH4OH in MeOH]/CH2Cl2) afforded 92 mg (43%) of a yellow foam.

後処理

  1. stirringthe solution was stirred at room temperature for 24 h
  2. stirringthe solution was stirred at room temperature for 24 h
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. washwashed with 25 mL of H2O and 1:1 satd
  5. extractionNaHCO3-brine solution which were back extracted with CH2Cl2 (3×30 mL) and EtOAc (1×30 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (silica gel, 7% [10% conc NH4OH in MeOH]/CH2Cl2)

出典と根拠

ORDレコード
ord-b08a472c539e49baa64bf29ab21c03c6
出典データセット
uspto-grants-2001_07
特許番号
US06265575B1

反応ノート

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