Ethylene Glycol → HCID 69052994, compound

HRID 1432556Notes

Reaction equation

HRID 1432556 reaction equation
[F:1][C:2]1[CH:8]=[C:7](I)[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:10][N:11]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(O)CO.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)(C)C.C(Cl)Cl.CO.[NH4+].[OH-].[Cu]I>[CH3:10][N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:7]2[CH:6]=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[CH:8]=2)[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 1856942-Fluoro-4-iodoanilineHCID 2283491-Methylhomopiperazine

Product 1

HCID 69052994HCID 69052994, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21896990Dichloromethane methanol ammonium hydroxideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-fluoro-4-iodoaniline (474 mg, 2.00 mmol), 1-methylhomopiperazine (0.372 mL, 3.00 mmol), ethylene glycol (0.222 mL, 4.00 mmol) and K3PO4 (848 mg, 4.00 mmol) in isopropanol (2 mL) was degassed with Ar before being charged with CuI (76 mg, 0.40 mmol). The mixture in a sealed tube was heated at 85° C. for three days. One fifth of the reaction mixture was applied to a silica gel prep TLC plate, which was then developed in CH2Cl2/MeOH/NH4OH (85/15/0.5). The area containing the desired product was scraped out, and the product was extracted out with CH2Cl2/MeOH (2/1) to give a solid (54 mg).

Workup

  1. customwas degassed with Ar

Sources & evidence

ORD record
ord-79222ea8596d4c4ba7fec1b3607097dc
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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