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

HRID 422873

반응식

HRID 422873 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4a540bd500c342bc81a6b30a89493bc1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101647B2

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