Potassium Carbonate → HCID 86593361, compound

HRID 1270799Notes

Reaction equation

HRID 1270799 reaction equation
[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1Br.[F:17][C:18]1[CH:24]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:22]=[CH:21][C:19]=1[NH2:20].C([O-])([O-])=O.[K+].[K+]>[Cu]I>[CH3:1][N:2]([CH3:16])[C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[CH:8]=[CH:7][C:6]=1[NH:20][C:19]1[CH:21]=[CH:22][C:23]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)=[CH:24][C:18]=1[F:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 20099591HCID 20099591, compoundHCID 68803105HCID 68803105, compound

Product 1

HCID 86593361HCID 86593361, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of N,N-dimethyl-2-bromo-5-cyclopropylphenylacetamide (1.0 g), 2-fluoro-4-(4-fluorophenyl)aniline (1.5 g), K2CO3 (490 mg), KI (590 mg), Cu (113 mg), CuI (337 mg) in xylenes (10 mL) is heated to reflux for 48 hours. After cooling, the reaction is filtered through silica gel and the filtrate concentrated to a brown oil. The oil is purified by flash chromatography using 10%, then 20%, then 30%, then 40% EtOAc in hexane to give the title product as a foam.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 48 hours
  3. temperatureAfter cooling
  4. filtrationthe reaction is filtered through silica gel
  5. concentrationthe filtrate concentrated to a brown oil
  6. customThe oil is purified by flash chromatography

Sources & evidence

ORD record
ord-58b526b3e60048f4a95f605268efd687
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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