Triethylamine → HCID 59164526, compound

HRID 1894038Notes

Reaction equation

HRID 1894038 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15].CCN(CC)CC.[CH3:24][O:25][CH2:26][C:27]#[CH:28]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([C:28]#[C:27][CH2:26][O:25][CH3:24])[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH2:15]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 693933-MethoxypropyneHCID 53436880Methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate

Product 1

HCID 59164526HCID 59164526, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (3.0 g, 8.69 mmol) and Et3N (22 mL) in dry dioxane (22 mL) was purged with argon during 15 min. (Ph3P)2PdCl2 (305 mg, 0.435 mmol), CuI (166 mg) and 3-methoxy-propyne (2.20 mL, 26.08 mmol) were added and the mixture was heated to 55° C. for 100 min. After cooling, the reaction mixture was filtered and the filtrate diluted with EtOAc, washed with water and brine and dried (Na2SO4). Evaporation of the volatiles gave a residue which was purified by MPLC (silica gel, cyclohexane/EtOAc 4:1) to yield the title compound (1.94 g, 78%) as a beige solid, m.p. 107-111° C.

Workup

  1. additionwere added
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. additionthe filtrate diluted with EtOAc
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the volatiles
  8. customgave a residue which
  9. customwas purified by MPLC (silica gel, cyclohexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-ae7af35feadc4f348f6981883933a07f
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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