2,4-Dichlorophenol → HCID 66917887, compound

HRID 1818009Notes

Reaction equation

HRID 1818009 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:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[OH:21].Cl.CN(C)CC(O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.[Cu]I>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[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 84492,4-DichlorophenolHCID 10796Cesium carbonateHCID 75605N,N-Dimethylglycine hydrochlorideHCID 534012037-Bromo-5-fluoro-3-methyl-1H-indole

Product 1

HCID 66917887HCID 66917887, 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 (1.60 g, 7.02 mmol) was reacted with 2,4-dichlorophenol (1.72 g, 10.5 mmol), CuI (134 mg, 0.702 mmol), N,N-dimethylglycine hydrochloride (293 mg, 2.10 mmol), and Cs2CO3 (4.57 g, 14.0 mmol) in anhydrous dioxane (14 mL). The crude product was purified by silica gel column chromatography utilizing a solvent system of 5% EtOAc/Hexanes to yield 746 mg of I-198B 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-bb2870dcaced4465a2ece16da8a84cff
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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