Sodium Bicarbonate → HCID 67310689、化合物

HRID 1401618ノート

反応式

HRID 1401618 の反応式
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:29][CH2:28][C:9]2[N:10]([CH2:18][C:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)(O)[CH3:20])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1.C(=O)(O)[O-].[Na+]>S(Cl)(Cl)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:29][CH2:28][C:9]2[N:10]([CH:18]=[C:19]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH3:20])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1

参加物

4

反応物 2

HCID 516892Sodium BicarbonateHCID 68486293HCID 68486293、化合物

生成物 1

HCID 67310689HCID 67310689、化合物収率 6.7%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒2 回

実験手順

1-[2-(3-Methoxy-propyl)-8-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-2-pyridin-4-yl-propan-2-ol (550 mg, 1.39 mmol) was dissolved in thionyl chloride (5 mL), stirred at RT for 1 h. Progress of the reaction was monitored by TLC/LCMS. After completion of the reaction, excess thionyl chloride was evaporated under vacuum. The solid mass obtained was neutralized with aqueous sodium bicarbonate and the desired compound extracted with EtOAc (100 mL×2). The organic layer was dried over anhydrous sodium sulfate, concentrated under vacuum to obtain crude product, which was purified by silica gel column chromatography (100-200 mesh) using MeOH: DCM (0-10%) as eluent followed by reverse phase HPLC to obtain 35 mg of 2-(3-Methoxy-propyl)-8-methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm): 8.62 (d, 2H), 7.42 (d, 2H), 7.22 (s, 1H), 7.10 (s, 1H), 7.0 (s, 2H), 3.80 (s, 2H), 3.50 (t, 2H), 3.36 (s, 3H), 2.92 (m, 2H), 2.78 (m, 4H), 2.42 (s, 3H), 2.02 (s, 3H), 1.95 (m, 2H). 1H NMR (CD3OD oxalate salt) δ (ppm): 8.82 (d, 2H), 8.30 (d, 2H), 7.80 (s, 1H), 7.38 (s, 1H), 7.16 (s, 2H), 4.40 (m, 1H), 3.98 (m, 1H), 3.60 (m, 4H), 3.50 (t, 2H), 3.40 (s, 3H), 3.25 (m, 2H), 2.42 (s, 3H), 2.20 (m, 2H), 2.18 (s, 3H).

後処理

  1. customwas evaporated under vacuum
  2. customThe solid mass obtained
  3. extractionthe desired compound extracted with EtOAc (100 mL×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto obtain crude product, which
  7. customwas purified by silica gel column chromatography (100-200 mesh)

出典と根拠

ORDレコード
ord-2e245da51db14c15be7188aab0229cff
出典データセット
uspto-grants-2014_12
特許番号
US08907097B2

反応ノート

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