Ethylenediamine → HCID 66616140, compound

HRID 2172143Notes

Reaction equation

HRID 2172143 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[CH:2]1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1.C(N)CN.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[F:16][C:17]([F:26])([F:25])[C:18]1[CH:23]=[CH:22][C:21]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=3)=[CH:2]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 61695Pentapotassium TriphosphateHCID 67993Benzene, 1-iodo-4-(trifluoromethyl)-HCID 66616139HCID 66616139, compound

Product 1

HCID 66616140HCID 66616140, compoundYield 52.7%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 4-(1H-pyrrol-3-yl)-benzoate (402 mg, 1.997 mmol, 1.0 eq.) and 4-trifluoromethyl-1-iodobenzene (652 mg, 2.39 mmol, 1.2 eq.) in anhydrous 1,4-dioxane (15 mL) is added copper(I) iodide (38 mg, 0.199 mmol, 0.1 eq.), ethylenediamine (13 μL, 0.199 mmol, 0.1 eq.) and potassium triphosphate (762 mg, 1.66 mmol, 3.31 eq.). The reaction mixture is degassed, flushed with nitrogen and heated to reflux for 18 hr. The reaction mixture is cooled, filtered and washed with ethyl acetate. The filtrate is concentrated and purified by silica gel chromatography (10% ethyl acetate/hexane) to get a white powder, methyl 4-[1-(4-trifluoromethyl-phenyl)-1H-pyrrol-3-yl]-benzoate (363.2 mg, 1.05 mmol, 52.7%). MS (ES+): m/e 345.11. 1H NMR (300 MHz, CDC3): δ 8.04 (2H, d, J=8 Hz), 7.72 (2H, d, J=8 Hz), 7.63 (2H, d, J=8 Hz), 7.54 (2H, d, J=8 Hz), 7.50 (1H, m), 7.18 (1H, m), 6.75 (1H, m), 3.93 (3H, s).

Workup

  1. customThe reaction mixture is degassed
  2. customflushed with nitrogen
  3. temperatureheated
  4. temperatureto reflux for 18 hr
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. washwashed with ethyl acetate
  8. concentrationThe filtrate is concentrated
  9. custompurified by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-52bd0098bb6d4de4aa02b1fc59d9a88a
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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