2-amino-N,6-dimethoxybenzamide → 2-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N,6-dimethoxybenzamide

HRID 288

Reaction equation

HRID 288 reaction equation
CONC(=O)c1c(N)cccc1OC.Cc1cc(Nc2cc(I)c(C(F)(F)F)cn2)n(C)n1>C1COCCO1.CC(=O)O.CC(=O)O.O=C([O-])[O-].[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CONC(=O)c1c(Nc2cc(Nc3cc(C)nn3C)ncc2C(F)(F)F)cccc1OC

Participants

7

Reactant 2

HCID 569516592-amino-N,6-dimethoxybenzamideHCID 67075489N-(1,3-dimethylpyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 569515502-[[2-[(2,5-dimethylpyrazol-3-yl)amino]-5-(trifluoromethyl)pyridin-4-yl]amino]-N,6-dimethoxybenzamideYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 634876Binap, (A+-)-CatalystHCID 4144353Palladium (II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(1,3-dimethyl-1H-pyrazol-5-yl)-4-iodo-5-(trifluoromethyl)pyridin-2-amine (50 mg, 0.13 mmol), 2-amino-N,6-dimethoxybenzamide (43.6 mg, 0.22 mmol), diacetoxypalladium (1.469 mg, 6.54 µmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (8.15 mg, 0.01 mmol) and cesium carbonate (85 mg, 0.26 mmol) were suspended in 1,4-dioxane (436 µl) and sealed into a microwave tube. The reaction was degased, purged with nitrogen and heated to 90 °C overnight => _slow reaction, a few expected product formed, no des-iodo observed, both SM left_ **_NOT ISOLATED_**

Sources & evidence

ORD record
ord-172edbc585f4482992d8b345126c6340
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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