Dimethyl Sulfoxide → HCID 53325403、化合物

HRID 2425518ノート

反応式

HRID 2425518 の反応式
[CH3:1][S:2]([CH3:4])=[O:3].CN(P(N(C)C)(N(C)C)=O)C.[Li]CCCC.Br[CH2:22][C:23]1[C:24]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[N:25][C:26]2[C:31]([C:32]=1[C:33]([NH:35][C@H:36]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:37][CH3:38])=[O:34])=[CH:30][CH:29]=[CH:28][CH:27]=2>C1COCC1>[CH3:1][S:2]([CH2:4][CH2:22][C:23]1[C:24]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[N:25][C:26]2[C:31]([C:32]=1[C:33]([NH:35][C@H:36]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:37][CH3:38])=[O:34])=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:3]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 12679HexamethylphosphoramideHCID 16064396HCID 16064396、化合物HCID 178418339Butyllithium

生成物 1

HCID 53325403HCID 53325403、化合物収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

A solution of DMSO (0.075 mL, 1.05 mmol) and HMPA (0.38 mL, 2.2 mmol) in anhydrous THF (3 mL) was prepared under N2 and cooled to −78° C. To this was added a solution of n-BuLi (0.71 mL, 1.6 M in hexanes, 1.13 mmol), the reaction allowed to stir for 10 min., then 3-(bromomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (8) (200 mg, 0.44 mmol) was added as a solution in anhydrous THF (1 mL). The reaction was allowed to stir 10 min., additional anhydrous THF (1 mL) added, and reaction allowed stirring another 10 min. The cooling bath was then removed, saturated aqueous NH4CI (1 mL), H2O (1 mL), and Et2O (1 mL) added, the layers shaken together, and then separated. The organics were then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/CH2Cl2) to give the desired product (170 mg, 85% yield) as a solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.10 (d, J=8.0 Hz, 1H), 7.86-7.61 (m, 2H), 7.55-7.25 (m, 12H), 5.29-5.16 (m, 1H), 3.44-3.07 (m, 2H), 2.73-2.37 (m, 2H), 2.27-2.15 (m, 3H), 2.15-1.86 (m, 2H), 1.02 (t, J=7.4 Hz, 3H); LCMS: m/z 457 (MH+). HRMS m/z 457.1927, calcd. 457.1950.

後処理

  1. stirringto stir 10 min.
  2. customreaction
  3. stirringallowed stirring another 10 min
  4. customThe cooling bath was then removed
  5. additionsaturated aqueous NH4CI (1 mL), H2O (1 mL), and Et2O (1 mL) added
  6. stirringthe layers shaken together
  7. customseparated
  8. dry with materialThe organics were then dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel chromatography (EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-99a970235e6f4b8594e3a5b859ad7c39
出典データセット
uspto-grants-2011_06
特許番号
US07964733B2

反応ノート

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