Water → HCID 3736321, compound

HRID 334996Notes

Reaction equation

HRID 334996 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4](Br)[C:3]=1[NH:11][C:12]([NH2:14])=[S:13].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].O>O1CCOCC1.[Cu]I>[NH2:14][C:12]1[S:13][C:4]2[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([Br:1])[C:3]=2[N:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 57695187HCID 57695187, compound

Product 1

HCID 3736321HCID 3736321, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A reaction mixture of (2) compound (1.3 g, 3.66 mmol), CuI (70 mg, 0.366 mmol, 0.1 eq.), 1,10-phenanthroline (70 mg, 0.366 mmol), and Cs2CO3 (1.8 g, 5.5 mmol, 1.5 eq.) in dioxane (20 mL) was stirred under reflux for 2 h under Ar. After cooling to room temperature, water (100 mL) was added; solid was filtered, washed with water (100 mL×3) followed by ether (50 mL×3). The solid was dried in vacuo at room temperature overnight, to provide 1 g (quantitative yield) of the desired product (3). 1H-NMR-(400 MHz, CDCl3)

Workup

  1. temperatureunder reflux for 2 h under Ar
  2. filtrationsolid was filtered
  3. washwashed with water (100 mL×3)
  4. customThe solid was dried in vacuo at room temperature overnight

Sources & evidence

ORD record
ord-634dde01ab3f4c3e86847931dd14e9f5
Source dataset
uspto-grants-2014_11
Patent number
US08883833B2

Reaction notes

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