Diethylamine → 1-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-5-{3-[2-(2-methoxy-ethoxy)-ethoxy]-prop-1-ynyl}-phthalazine

HRID 2268929Notes

Reaction equation

HRID 2268929 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][C:10]#[CH:11].[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:40])[C:18]=1[CH2:19][C:20]1[C:29]2[C:24](=[C:25](OS(C(F)(F)F)(=O)=O)[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[CH:23]=[N:22][N:21]=1.C(NCC)C>C(OCC)C.[Cu]I>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:40])[C:18]=1[CH2:19][C:20]1[C:29]2[C:24](=[C:25]([C:11]#[C:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[CH:23]=[N:22][N:21]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 183816833-[2-(2-Methoxyethoxy)ethoxy]prop-1-yneHCID 53981658Trifluoro-methanesulfonic acid 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl ester

Product 1

HCID 183816641-(3,5-Dichloro-pyridin-4-ylmethyl)-6-methoxy-5-{3-[2-(2-methoxy-ethoxy)-ethoxy]-prop-1-ynyl}-phthalazineYield 46.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A suspension under N2 of 3-[2-(2-methoxy-ethoxy)-ethoxy]-propyne (810 mg, 5.12 mmoles), prepared as described in example 133, trifluoro-methanesulfonic acid 1-(3,5-dichloro-pyridin-4-ylmethyl)-6-methoxy-phthalazin-5-yl ester (2 g, 4.27 mmoles), prepared as described in example 73, and diethylamine (40 ml) was added under stirring with bis(triphenylphosphine)PdCl2 (60 mg, 0.085 mmole) and CuI (16.18 mg, 0.085 mmole). The mixture was refluxed for 6 hours, then dried. The residue was flash chromatographed (eluent: ethyl acetate) to give a solid which was taken up in ethyl ether, filtered and dried under vacuum, at 40° C. to give 940 mg of the title compound (yield: 46%).

Workup

  1. customprepared
  2. additionwas added
  3. temperatureThe mixture was refluxed for 6 hours
  4. customdried
  5. customchromatographed (eluent: ethyl acetate)
  6. customto give a solid which
  7. filtrationfiltered
  8. customdried under vacuum, at 40° C.

Sources & evidence

ORD record
ord-9316a6173ad842faa4144087ad282a5a
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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