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Cesium carbonate → tert-Butyl 5-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710304
ノート
印刷プレビュー

反応式

HRID 710304 の反応式
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11]Cl)[O:10][C:6]=2[CH:5]=[C:4]([Cl:13])[CH:3]=1.[OH:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:30][O:29][C:28]([CH3:32])([CH3:31])[O:27][CH2:26]1)[CH2:19][CH2:18]2.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)C>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][O:14][C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][C:25]3([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:30][O:29][C:28]([CH3:32])([CH3:31])[O:27][CH2:26]3)[CH2:19][CH2:18]4)[O:10][C:6]=2[CH:5]=[C:4]([Cl:13])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 667262474,6-Dichloro-2-(chloromethyl)benzofuranHCID 66726286tert-Butyl 5-((5-hydroxyindolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

生成物 1

HCID 86661762tert-Butyl 5-((5-((4,6-dichlorobenzofuran-2-yl)methoxy)indolin-1-yl)methyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate収率 41.2%

試薬・触媒・溶媒 2

HCID 3283
Diethyl Ether
溶媒
HCID 6228Dimethylformamide溶媒

実験手順

A mixture of the product of Step F (0.05 g; 0.21 mmol) and the product of Step C (0.08 g; 0.21 mmol) and Cs2CO3 (0.07 g; 0.21 mmol) in anhydrous DMF (1 ml) was stirred overnight at room temperature under N2. This was diluted to 10 ml with diethyl ether, washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; hexane/EtOAc 7:3), to give the title compound (0.05 g; 41%) as a brownish syrup. 1H-NMR (CDCl3) 1.44 (m, 15H); 2.95 (tr, 2H, J=8.5 Hz); 3.41 (tr, 2H, J=8.5 Hz); 3.45 (5, 2H); 3.87-4.01 (m, 4H); 4.69 (broad s, 1H); 5.03 (s, 2H); 6.49 (d, 1H, J=8.5 Hz); 6.69 (dd, 1H, J=2.5, 8.5 Hz); 6.79 (s, 2H); 7.23 (s, 1H, J=2.5 Hz); 7.39 (s, 1H).

後処理

  1. washwashed with H2O, brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was purified by FCC (SiO2; hexane/EtOAc 7:3)

出典と根拠

ORDレコード
ord-edf48cb64c544a0fa314bb5f31a1c361
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

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