2-Chloro-5-iodopyridin-4-amine → HCID 59578429, compound

HRID 391317Notes

Reaction equation

HRID 391317 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5](I)=[CH:4][N:3]=1.[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([C:19]#[CH:20])[CH:16]=[N:15][CH:14]=1>[Cu]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.C(N(CC)CC)C>[CH3:10][O:11][C:12](=[O:21])[C:13]1[CH:18]=[C:17]([C:19]#[C:20][C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][C:6]=2[NH2:8])[CH:16]=[N:15][CH:14]=1

Participants

6

Reactant 2

HCID 454803662-Chloro-5-iodopyridin-4-amineHCID 53898384Methyl 5-ethynylnicotinate

Product 1

HCID 59578429HCID 59578429, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A 250 mL round bottom flask flushed with N2 was charged with 2-chloro-5-iodo-pyridin-4-ylamine (1.00 g, 3.93 mmol), 5-ethynyl-nicotinic acid methyl ester (0.633 g, 3.93 mmol), copper(I) iodide (0.037 g, 0.196 mmol), bis(triphenylphosphine)palladium(II) chloride (0.138 g, 0.196 mmol) and triethyl amine (50 mL). The reaction mixture was stirred at 100° C. for 3 h. The reaction was cooled to room temperature, filtered and the precipitate washed thoroughly with ethyl acetate. The filtrate was washed with water twice. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford crude product 5-(4-amino-6-chloro-pyridin-3-ylethynyl)-nicotinic acid methyl ester as a brown solid which was taken onto next step without any purification. ESI-MS: m/z 288.0 (M+H)+

Workup

  1. customA 250 mL round bottom flask flushed with N2
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe precipitate washed thoroughly with ethyl acetate
  5. washThe filtrate was washed with water twice
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e01a748df14948058b125d1ebfc03ec4
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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