Potassium Carbonate → HCID 86760841, compound

HRID 2108539Notes

Reaction equation

HRID 2108539 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])=[O:4].C([O-])([O-])=O.[K+].[K+].[OH-].[K+].[CH2:27](Br)[CH:28]=[CH:29][CH3:30]>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CCOCC>[CH2:27]([N:5]([CH2:6][CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[I:16])[C:3](=[O:4])[C:2]([F:1])([F:17])[F:18])[CH:28]=[CH:29][CH3:30]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 1224142-Butene, 1-bromo-HCID 222927722,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide

Product 1

HCID 86760841HCID 86760841, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N-trifluoroacetyl-2-iodo-5-methoxyphenethylamine (6.68 g, 17.9 mmol) in toluene (100 mL) was treated with K2CO3 (3.22 g, 23.3 mmol), KOH (3.01 g, 53.7 mmol), n-Bu4NBr (0.580 g, 1.80 mmol) and crotyl bromide (3.15 g, 23.3 mmol). The mixture was stirred at 75 C for 16 hours, cooled to 20 C, diluted with Et2O (500 mL), washed with 10% aqueous HCl (500 mL) and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 5.22 g of a clear oil. MS calculated for C15H17F3INO2+H: 428, observed: 428.

Workup

  1. temperaturecooled to 20 C
  2. washwashed with 10% aqueous HCl (500 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6e76c417142d4c78b49d19aea9462994
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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