Propyne → HCID 69343046, compound

HRID 855262Notes

Reaction equation

HRID 855262 reaction equation
[CH:1]#[C:2][CH3:3].[CH3:4][O:5][C:6](=[O:16])[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9](I)[C:8]=1[NH2:15]>C(N(CC)CC)C.[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:4][O:5][C:6](=[O:16])[C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([C:1]#[C:2][CH3:3])[C:8]=1[NH2:15]

Participants

6

Reactant 2

HCID 6335PropyneHCID 7020924Methyl 2-amino-5-chloro-3-iodobenzoate

Product 1

HCID 69343046HCID 69343046, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

Propyne (excess ca 3 ml) was condensed onto a cold (−78° C.) solution of 2-amino-5-chloro-3-iodobenzoic acid methyl ester (500 mg, 1.61 mmol) in triethylamine (10 ml) in a Parr pressure reaction vessel. To this solution was added copper (I) iodide and bis(triphenylphosphine)palladium (II) chloride and the pressure tube was then sealed and stirred at rt for 4 h. The solvent was then removed in vacuo and the residue was purified by flash column chromatography (9:1 cyclohexane:EtOAc) to give 2-amino-5-chloro-3-prop-1-ynylbenzoic acid methyl ester (340 mg, 95%) as an off white solid. 1H NMR (CDCl3, 300 MHz): δ 7.76 (d, J=2.5 Hz, 1H), 7.33 (d, J=2.5 Hz, 1H), 6.37 (br s, 2H), 3.87 (s, 3H), 2.13 (s, 3H).

Workup

  1. customin a Parr pressure reaction vessel
  2. customthe pressure tube was then sealed
  3. customThe solvent was then removed in vacuo
  4. customthe residue was purified by flash column chromatography (9:1 cyclohexane:EtOAc)

Sources & evidence

ORD record
ord-5357e71cba85450f9c7c33b6765dd9e4
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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