Diethyl Ether → HCID 54504767, compound

HRID 850624Notes

Reaction equation

HRID 850624 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]([NH:16][CH2:17][C:18]#[CH:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:20][CH2:21][O:22]CC>C(N(CC)CC)C.[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:12]([O:11][C:9](=[O:10])[N:16]([CH2:17][CH2:18][CH2:19][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1)[CH2:20][CH:21]=[O:22])([CH3:13])([CH3:14])[CH3:15]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 122742,6-DibromopyridineHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 54504767HCID 54504767, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
0 °C

Procedure

A solution of 2,6-dibromopyridine 20-1 (111 g, 468 mmol) and N-BOC-propargylamine (80.0 g, 515 mmol) in 500 ml of triethylamine at 0° C. was treated with copper(I) iodide (2.23 g, 11.7 mmol). The mixture was purged with argon and then dichlorobis(triphenylphosphine)-palladium(II) 8.22 g, 11.7 mmol) was added. The solution was stirred at 0° C. for one hour, then at room temperature for 16 hours. The solution was diluted with 250 mL ether and washed with H2O (4×100 mL). The organic extract was washed with brine and dried over Na2SO4. The solvents were removed in vacuo and the crude product was purified by silica gel chromatography (25% EtOAc/hexane) to afford 20-2.

Workup

  1. customThe mixture was purged with argon
  2. waitat room temperature for 16 hours
  3. washwashed with H2O (4×100 mL)
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvents were removed in vacuo
  8. customthe crude product was purified by silica gel chromatography (25% EtOAc/hexane)
  9. customto afford 20-2

Sources & evidence

ORD record
ord-aaa93a6aef8e459cb853c45b80b7a59d
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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