2-Bromo-4-nitroanisole → 5-chloro-N-(2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine

HRID 419

Reaction equation

HRID 419 reaction equation
COc1ccc([N+](=O)[O-])cc1Br.Nc1ncc(Cl)c(-c2cnn3ccccc23)n1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>COc1ccc([N+](=O)[O-])cc1Nc1ncc(Cl)c(-c2cnn3ccccc23)n1

Participants

7

Reactant 2

HCID 788702-Bromo-4-nitroanisoleHCID 1414749585-Chloro-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amine

Product 1

HCID 732925485-chloro-N-(2-methoxy-5-nitrophenyl)-4-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-2-amineYield 4%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

_Crude SM used_ 2-bromo-1-methoxy-4-nitrobenzene (0.029 g, 0.13 mmol), 5-chloro-4-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine (0.031 g, 0.125 mmol) and cesium carbonate (0.057 g, 0.18 mmol) were suspended in dry dioxane (2 mL) the mixture degassed with nitrogen for 10 minutes. TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (6.87 mg, 7.50 µmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (5.79 mg, 10.00 µmol) were added and the mixture was sealed into a microwave tube. The reaction was heated to 150 °C for 2 hours in the microwave reactor and cooled to RT. Possibly product - not very much. The reaction was heated to 150 °C for 10 hours in the microwave reactor and cooled to RT. Product now c4%, both starting materials still present. Not continued.

Sources & evidence

ORD record
ord-75e934c9ac8c4736a342c35dfcb5f15c
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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