Triethylamine → HCID 66680965, compound

HRID 1626763Notes

Reaction equation

HRID 1626763 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=2)=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[CH:29]1([C:35]#[CH:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>CN(C=O)C.C(OCC)(=O)C.[Cu](I)I.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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:36]#[C:35][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:16]=2)=[O:14])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 63524758HCID 63524758, compound

Product 1

HCID 66680965HCID 66680965, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g (1.2 mmol) of methyl 5-chloro-2-{[(3-iodophenyl)carbonyl]amino}benzoate obtained in Example 63-(i), 146 mg (1.4 mmol) of triethylamine, 11.5 mg (0.06 mmol) of copper iodide, 25 mg (0.036 mmol) of bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2), and 208 mg (1.92 mmol) of cyclohexylacetylene were stirred in DMF (10 mL) at room temperature for 21 hours. The reaction mixture was diluted with ethyl acetate, and washed with H2O, diluted hydrochloric acid, aqueous saturated sodium hydrogen carbonate solution, and saturated saline in this order. Thereafter, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 169 mg of methyl 5-chloro-2-({[3-(cyclohexylethynyl)phenyl]carbonyl}amino)benzoate (yield: 36%).

Workup

  1. washwashed with H2O, diluted hydrochloric acid, aqueous saturated sodium hydrogen carbonate solution, and saturated saline in this order
  2. dry with materialThereafter, the organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained crude product
  5. customwas separated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-3d0bab78ef234905b83ebd03a2ef5986
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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