Cesium carbonate → 6-[2-(dimethylamino)ethoxy]-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 422873

反応式

HRID 422873 の反応式
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3([CH2:22][O:23][C:8]=2[CH:7]=1)[C:20]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:14][C:13]3=[O:21].CC1C=CC(S(O[CH2:36][C@H:37]2[CH2:41][CH2:40][CH2:39][O:38]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(=O)CC>[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3([CH2:22][O:23][C:8]=2[CH:7]=1)[C:20]1[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=1)[N:14]([CH2:36][C@H:37]1[CH2:41][CH2:40][CH2:39][O:38]1)[C:13]3=[O:21]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 7033050(R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonateHCID 452801616-[2-(dimethylamino)ethoxy]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

生成物 1

HCID 452802206-[2-(dimethylamino)ethoxy]-1'-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one収率 76.5%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

To a stirred solution of 6-[2-(dimethylamino)ethoxy]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.21 g, 0.64 mmol) in 2-butanone (10 mL) was added (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate (0.20 g, 0.76 mmol) followed by cesium carbonate (0.63 g, 1.90 mmol) at 0° C. The mixture was stirred at ambient temperature for 16 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was subjected to column chromatography (ethyl acetate/methanol/ammonium hydroxide, 10/1/0.2) to give 6-[2-(dimethylamino)ethoxy]-1′-[(2R)-tetrahydrofuran-2-ylmethyl]spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (0.20 g, 76%): 1H NMR (300 MHz, CDCl3) δ 7.31-7.24 (m, 1H), 7.14-6.96 (m, 3H), 6.57 (d, J=8.3 Hz, 1H), 6.52 (d, J=2.2 Hz, 1H), 6.36 (dd, J=8.3, 2.2 Hz, 1H), 4.91 (d, J=9.0 Hz, 1H), 4.66 (d, J=9.0 Hz, 1H), 4.31-4.19 (m, 1H), 4.00 (t, J=5.8 Hz, 2H), 3.94-3.63 (m, 4H), 2.68 (t, J=5.8 Hz, 2H), 2.97 (s, 6H), 2.09-1.63 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 178.1, 177.9, 162.0, 160.7, 142.9, 142.8, 132.5, 132.4, 128.7, 128.6, 123.7, 123.6, 123.5, 123.4, 123.2, 121.1, 121.0, 109.6, 109.4, 108.1, 97.2, 80.6, 80.5, 68.24, 68.2, 66.3, 58.2, 57.5, 45.9, 44.6, 44.5, 29.2, 28.9, 25.7, 25.5; MS (ES+) m/z 409.3 (M+1).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-4a540bd500c342bc81a6b30a89493bc1
出典データセット
uspto-grants-2012_01
特許番号
US08101647B2

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