Tetrahydrofuran → HCID 86618221, compound

HRID 1673264Notes

Reaction equation

HRID 1673264 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13](C1C2C=CC=C(N)C=2C=CC=1)[C:14]1([C:17]([F:20])([F:19])[F:18])[CH2:16][O:15]1.[Cl-].[NH4+:33].[CH2:34]1[CH2:38]O[CH2:36][CH2:35]1>C(OCC)C.[Cu]I>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([C:2]1[CH:1]=[CH:9][C:8]2[C:35](=[CH:34][CH:38]=[CH:12][CH:7]=2)[C:36]=1[NH2:33])[C:14]1([C:17]([F:18])([F:19])[F:20])[CH2:16][O:15]1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 86618220HCID 86618220, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86618221HCID 86618221, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

To 30 mg (0.16 mmol) copper(I)iodide in 2 ml THF at −30° C. are added 0.71 ml of a 3M ethyl magnesium bromid in diethyl ether. After 30 minutes at −30° C. 200 mg (0.54 mmol) {[2-methoxyphenyl][2-(trifluoromethyl)oxiranyl]methyl}naphthalene-5-amine in 0.5 ml THF are added. The reaction mixture is stirred for 2 hours while warmed to −10° C. and then poured into a saturated ammonium chloride solution. Phases are separated and the aqueous layer is extracted twice with ethyl acetate. The combined organic phases are washed with brine, died over sodium sulphate and evaporated. Flash chromatography on silica gel (ethyl acetate in hexane 10% to 50%) yields 12 mg of the title compound.

Workup

  1. customPhases are separated
  2. extractionthe aqueous layer is extracted twice with ethyl acetate
  3. washThe combined organic phases are washed with brine
  4. customevaporated

Sources & evidence

ORD record
ord-aa12a2b749b74c349e4b9ede48fff599
Source dataset
uspto-grants-2011_08
Patent number
US07999108B2

Reaction notes

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