Triethylamine → 5-(3,3-Diethoxy-1-propynyl)-2-(3,4-difluorophenyl)pyridine

HRID 2399210Notes

Reaction equation

HRID 2399210 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)=[N:6][CH:7]=1.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[C:20]#[CH:21])[CH3:17].C(N(CC)CC)C>C(OCC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]Br>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[C:20]#[C:21][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)=[N:6][CH:7]=1)[CH3:17]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 662853,3-DiethoxypropyneHCID 193864195-Bromo-2-(3,4-difluorophenyl)pyridine

Product 1

HCID 193865395-(3,3-Diethoxy-1-propynyl)-2-(3,4-difluorophenyl)pyridine

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.00 g of crude 5-bromo-2-(3,4-difluorophenyl)pyridine (GC purity 81%), 1.12 ml of 3,3-diethoxy-1-propine, 0.138 g of tetrakis(triphenylphosphine)palladium, 0.052 g of copper(I) bromide and 36 ml of triethylamine was heated to boiling for 2 hours. After cooling the reaction mixture was diluted with 100 ml of diethyl ether, washed twice with 40 ml of water each time, dried over sodium sulphate, filtered, the filtrate was boiled briefly with active charcoal, filtered and concentrated. The crude 5-(3,3-diethoxy-1-propynyl)-2-(3,4-difluorophenyl)pyridine, (2.58 g; GC purity 72%), obtained as a brown-black oil, was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureAfter cooling the reaction mixture
  3. washwashed twice with 40 ml of water each time
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b03f24197592429e8aed2021d1b757d3
Source dataset
uspto-grants-1995_09
Patent number
US05447657

Reaction notes

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