4-Ethynylaniline → 5-[(4-aminophenyl)ethynyl]-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

HRID 2373185Notes

Reaction equation

HRID 2373185 reaction equation
Br[C:2]1[N:3]=[C:4]([C:9]2[N:10]([CH2:18][CH3:19])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][C:12]=3[N:17]=2)[C:5]([NH2:8])=[N:6][CH:7]=1.[C:20]([C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1)#[CH:21]>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)I.C(N(CC)CC)C>[NH2:26][C:25]1[CH:27]=[CH:28][C:22]([C:20]#[C:21][C:2]2[N:3]=[C:4]([C:9]3[N:10]([CH2:18][CH3:19])[C:11]4[CH:16]=[CH:15][N:14]=[CH:13][C:12]=4[N:17]=3)[C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 2

HCID 37600254-EthynylanilineHCID 598524085-bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Product 1

HCID 98415725-[(4-aminophenyl)ethynyl]-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

5-Bromo-3-(1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)pyrazin-2-amine (0.051 g, 0.16 mmol) (made in example 2), 4-ethynylaniline (0.060 g, 0.51 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.006 g, 0.009 mmol), copper iodide (0.004 g, 0.02 mmol) and triethyl amine (3 mL) were combined and subjected to 180° C. for 1 hr in a SmithSynthesizer microwave. The resulting mixture is treated with silica gel, and the volatiles removed in vacuo. The title compound is obtained by silica gel chromatography (0.004 g).

Workup

  1. additionThe resulting mixture is treated with silica gel
  2. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-287799b20059480f87a8c93586cccce1
Source dataset
uspto-grants-2008_12
Patent number
US07459454B2

Reaction notes

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