Potassium Carbonate → HCID 86760842, compound

HRID 2108542Notes

Reaction equation

HRID 2108542 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+].Br[CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31]>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CCOCC>[CH3:31][C:30]([CH3:32])=[CH:29][CH2:28][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]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 700922-Butene, 1-bromo-3-methyl-HCID 222927722,2,2-Trifluoro-N-[2-(2-iodo-5-methoxyphenyl)ethyl]acetamide

Product 1

HCID 86760842HCID 86760842, compoundYield 32.8%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of N-trifluoroacetyl-2-iodo-5-methoxyphenethylamine (0.700 g, 1.88 mmol) in toluene (25 mL) was treated with K2CO3 (0.340 g, 2.4 mmol), KOH (0.210 g, 3.76 mmol), n-Bu4NBr (0.060 g, 0.19 mmol) and 4-bromo-2-methyl-2-butene (0.364 g, 2.44 mmol). The mixture was stirred at 80 C for 3 hours, cooled to 20 C, diluted with ether (100 mL), washed with 10% HCl (50 mL) and concentrated. Flash chromatography (10% EtOAc in hexane, silica) resulted in 0.272 g of a clear oil. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.65 (m, 1H), 6.75 (m, 1H), 6.54 (m, 1H), 5.20 (m, 0.4H), 5.0 (m, 0.6H), 4.10 (m, 1H), 3.82 (m, 1H), 3.76 (d, 2H), 3.50 (m, 2H), 3.02 (m, 2H), 1.75 (m, 3H), 1.66(m, 3H).

Workup

  1. temperaturecooled to 20 C
  2. washwashed with 10% HCl (50 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-725d919624734028842eab5d7ff0bdf1
Source dataset
uspto-grants-2009_04
Patent number
US07514422B2

Reaction notes

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