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 710304Notes

Reaction equation

HRID 710304 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-edf48cb64c544a0fa314bb5f31a1c361
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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