2,5-Dibromopyridine → N-[3-(5-Bromopyridin-2-yl)prop-2-ynyl]acetamide

HRID 49566Notes

Reaction equation

HRID 49566 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]([NH:12][CH2:13][C:14]#[CH:15])(=[O:11])[CH3:10]>C(NC(C)C)(C)C.C(OCC)(=O)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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]#[C:14][CH2:13][NH:12][C:9](=[O:11])[CH3:10])=[N:3][CH:4]=1

Participants

7

Reactant 2

HCID 693532,5-DibromopyridineHCID 24079665881-41-6

Product 1

HCID 12991110N-[3-(5-Bromopyridin-2-yl)prop-2-ynyl]acetamideYield 89.7%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,5-dibromopyridine (1-1) (1.19 g), N-acetyl-propargylamine (733 mg), CuI (10 mg), and Pd(PPh3)2Cl2 (73 mg) in diisopropylamine (20 mL) was stirred at ambient temperature under nitrogen atmosphere over 3 days. The mixture was diluted with ethyl acetate (50 mL). The solid was filtered and washed with ethyl acetate. The filtrate and wash were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate as eluant to give crystalline 1-2 (1.14 g).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with ethyl acetate
  3. washThe filtrate and wash
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-20010559d84d49ec8985a26d4a1dbf05
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

Loading…