2,5-Dibromopyridine → N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamide

HRID 49572Notes

Reaction equation

HRID 49572 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[CH:9]([NH:11][CH2:12][C:13]#[CH:14])=[O:10]>C(NC(C)C)(C)C.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.[Cu]I>[CH:9]([NH:11][CH2:12][C:13]#[C:14][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][CH2:12][NH:11][CH:9]=[O:10])=[N:3][CH:4]=1)=[O:10]

Participants

6

Reactant 2

HCID 693532,5-DibromopyridineHCID 985544514502-66-0

Product 1

HCID 11413798N-(3-{5-[3-(Formamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)formamideYield 93.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 7912DiisopropylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,5-dibromopyridine (100 g), N-formylpropargylamine (87.7 g), PdCl2(PPh3)2 (2.96 g), and CuI (0.2 g) in diisopropylamine (3 L) was heated at 70° C. for 6 h under a nitrogen atmosphere. The mixture was cooled to 20-22° C. and filtered. The cake was dried and then slurried in water (3 L) at 0-5° C. for 3 h. The slurry was filtered, and the cake was dried to afford 95.4 g of the title compound 9-1.

Workup

  1. temperatureThe mixture was cooled to 20-22° C.
  2. filtrationfiltered
  3. customThe cake was dried
  4. filtrationThe slurry was filtered
  5. customthe cake was dried

Sources & evidence

ORD record
ord-b6477a3ab4f04f7c91bc20db956d3175
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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