3-Methoxypropyne → HCID 23156218, compound

HRID 252341Notes

Reaction equation

HRID 252341 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2I.[CH3:13][O:14][CH2:15][C:16]#[CH:17]>CN(C)C=O.C(N(CC)CC)C.O.[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>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[N:6]=[C:5]2[C:17]#[C:16][CH2:15][O:14][CH3:13]

Participants

8

Reactant 2

HCID 693933-MethoxypropyneHCID 231562265-bromo-3-iodo-1-methyl-1H-indazole

Product 1

HCID 23156218HCID 23156218, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 81.67 g of 5-bromo-3-iodo-1-methyl-1H-indazole in 750 ml of N,N-dimethylformamide and 335 ml of triethylamine is admixed at room temperature under argon with 25 ml of 3-methoxypropyne, 5.5 g of copper(I) iodide and 10 g of bis(triphenylphosphine)palladium(II) chloride, and subsequently heated to 60° C. After 1 hour, the reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate (4×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.67 (2:1 EtOAc-heptane). Rt=4.42 (gradient I).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate (4×)
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-a8f90e61a1e54e63b8cd5e5ce3954a41
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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