Triethylamine → 3-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine

HRID 1435586Notes

Reaction equation

HRID 1435586 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[CH:13])[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C.[NH2:21][C:22]1[C:27](Br)=[CH:26][C:25]([N+:29]([O-:31])=[O:30])=[CH:24][N:23]=1>O1CCCC1.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][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]#[C:13][C:27]2[C:22]([NH2:21])=[N:23][CH:24]=[C:25]([N+:29]([O-:31])=[O:30])[CH:26]=2)[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27344122-Amino-3-bromo-5-nitropyridineHCID 714077821-Ethynyl-3-(2-methoxyethoxy)benzene

Product 1

HCID 684671423-[3-(2-Methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamineYield 74.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-(2-Methoxy-ethoxy)-phenylacetylene (6.3 g, 36 mmol) was added to a solution of triethylamine (1.92 mL, 14 mmol), 2-amino-3-bromo-5-nitropyridine (4 g, 18 mmol), PdCl2(PPh3)2 (966 mg, 1.38 mmol) and CuI (262 mg, 1.38 mmol) in anhydrous tetrahydrofuran (80 mL) in the dark. The mixture was stirred at room temperature for 48 hours then concentrated in vacuo and dissolved in dichloromethane (150 mL). The organic solution was washed with water (25 mL), dried over MgSO4, filtered and concentrated in vacuo to 20% of its original volume and heptane (20 mL) was then added. The resultant yellow solid was filtered and dried to give 3-[3-(2-methoxy-ethoxy)-phenylethynyl]-5-nitro-pyridin-2-ylamine (4.2 g, 74% yield).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutiondissolved in dichloromethane (150 mL)
  3. washThe organic solution was washed with water (25 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to 20% of its original volume and heptane (20 mL)
  7. additionwas then added
  8. filtrationThe resultant yellow solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-d8566e4f216b46c6a0eb2ad4d1d9638a
Source dataset
uspto-grants-2009_11
Patent number
US07618964B2

Reaction notes

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