3-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine → 1-[4-[4-[(5-Chloro-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,5-dimethoxyphenyl]piperazin-1-yl]ethanone

HRID 113

Reaction equation

HRID 113 reaction equation
COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1N.Clc1ncc(Cl)c(-c2cnc3ccccn23)n1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>COc1cc(N2CCN(C(C)=O)CC2)c(OC)cc1Nc1ncc(Cl)c(-c2cnc3ccccn23)n1

Participants

7

Reactant 2

HCID 469346053-(2,5-Dichloropyrimidin-4-yl)imidazo[1,2-a]pyridineHCID 685924151-(4-(4-Amino-2,5-dimethoxyphenyl)piperazin-1-yl)ethanone

Product 1

HCID 453819881-[4-[4-[(5-Chloro-4-imidazo[1,2-a]pyridin-3-ylpyrimidin-2-yl)amino]-2,5-dimethoxyphenyl]piperazin-1-yl]ethanoneYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

_3-(2,5-dichloropyrimidin-4-yl)imidazo[1,2-a]pyridine (132.5 mg, 0.50 mmol)_ _ _ _1-(4-(4-amino-2,5-dimethoxyphenyl)piperazin-1-yl)ethanone (140 mg, 0.50 mmol)_ ___(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (23.14 mg, 0.04 mmol)_ _ _ _cesium carbonate (244 mg, 0.75 mmol)_ ___diacetoxypalladium (4.49 mg, 0.02 mmol)_ _were suspended in_ _1,4-dioxane (4 ml)_ _,degased with argon . The mixture was heated to_ _80 °C_ _ for 2 hrs *_

Sources & evidence

ORD record
ord-ea73803169b640e3b40a2b6127b91b44
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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