3,4-Dichlorophenol → HCID 66917847, compound

HRID 1818010Notes

Reaction equation

HRID 1818010 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].Cl.CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11]

Participants

7

Reactant 4

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 534012037-Bromo-5-fluoro-3-methyl-1H-indole

Product 1

HCID 66917847HCID 66917847, compoundYield 34%

Reagents, catalysts & solvents 2

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

Procedure

Following general method A-18, 7-Bromo-5-fluoro-3-methyl-1H-indole (727 mg, 3.19 mmol) was reacted with 3,4-dichlorophenol (779 mg, 4.78 mmol), CuI (60.8 mg, 0.319 mmol), N,N-dimethylglycine hydrochloride (134 mg, 0.957 mmol), and Cs2CO3 (2.07 g, 6.38 mmol) in anhydrous dioxane (6.4 mL). The crude product was purified by silica gel column chromatography utilizing a solvent system of 5% EtOAc/Hexanes to yield 506 mg of I-198C as a yellow oil (34%). 1H NMR (400 MHz, CDCl3).

Workup

  1. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-380f56c4543547e8a7556bdc9dbaf4b8
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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