1-Methylpiperazine → N-[5-(1H-imidazol-2-yl)-2-methylphenyl]-4-[[3-(4-methylpiperazin-1-yl)-2-pyridinyl]methoxy]benzamide

HRID 597

Reaction equation

HRID 597 reaction equation
CN1CCNCC1.Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2Br)cc1>CC(=O)N(C)C.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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>Cc1ccc(-c2ncc[nH]2)cc1NC(=O)c1ccc(OCc2ncccc2N2CCN(C)CC2)cc1

Participants

7

Reactant 2

HCID 531671-MethylpiperazineHCID 1412335914-[(3-bromo-2-pyridinyl)methoxy]-N-[5-(1H-imidazol-2-yl)-2-methylphenyl]benzamide

Product 1

HCID 68744892N-[5-(1H-imidazol-2-yl)-2-methylphenyl]-4-[[3-(4-methylpiperazin-1-yl)-2-pyridinyl]methoxy]benzamideYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(5-(1H-imidazol-2-yl)-2-methylphenyl)-4-((3-bromopyridin-2-yl)methoxy)benzamide (50 mg, 0.11 mmol), 1-methylpiperazine (32.4 mg, 0.32 mmol), Pd2(dba)3 (19.76 mg, 0.02 mmol) and BINAP (26.9 mg, 0.04 mmol), CS2CO3 (70.3 mg, 0.22 mmol) in DMA (5 mL) was stirred at 100 °C for overnight. LCMS didn't mornitor the desired product.

Sources & evidence

ORD record
ord-18a5ade19723420ab980b1bccfb56a9b
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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