Dichloromethane → HCID 67023410, compound

HRID 1670721Notes

Reaction equation

HRID 1670721 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH:22]([CH2:27][CH2:28][CH3:29])[CH2:21][C:20]=3[NH:19][C:18]([CH3:30])=[C:17]2[C:31]#[N:32])[CH:5]=[C:6]([O:13][CH2:14][CH3:15])[C:7]=1[O:8]S(C)(=O)=O.F[C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH:22]([CH2:27][CH2:28][CH3:29])[CH2:21][C:20]=3[NH:19][C:18]([CH3:30])=[C:17]2[C:31]#[N:32])[CH:5]=[C:6]([O:13][CH2:14][CH3:15])[C:7]=1[O:8][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 86633609HCID 86633609, compound

Product 1

HCID 67023410HCID 67023410, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the product of step b (0.20 g), 1-fluoro-4-nitrobenzene (53 μL) and cesium carbonate (0.22 g) was dissolved in dimethyl sulfoxide (1 mL) and stirred at 80° C. for 16 h. Dichloromethane was added and the reaction mixture was washed with a solution of 1% hydrochloric acid in water and with saturated brine. The organic phase was concentrated and the title compound was obtained after flash column chromatography (silica gel, heptane/ethyl acetate).

Workup

  1. washthe reaction mixture was washed with a solution of 1% hydrochloric acid in water and with saturated brine
  2. concentrationThe organic phase was concentrated

Sources & evidence

ORD record
ord-d74eda88ad3f40f08b4cd0258fa71486
Source dataset
uspto-grants-2011_08
Patent number
US07994189B2

Reaction notes

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