Methylamine hydrochloride → N-methyl-5-(trifluoromethyl)pyridin-3-amine

HRID 182

Reaction equation

HRID 182 reaction equation
CN.Cl.FC(F)(F)c1cncc(Br)c1>C1COCCO1.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.ClC(Cl)Cl.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]>CNc1cncc(C(F)(F)F)c1

Participants

7

Reactant 2

HCID 6364545Methylamine hydrochlorideHCID 111279913-Bromo-5-(trifluoromethyl)pyridine

Product 1

HCID 21221268N-methyl-5-(trifluoromethyl)pyridin-3-amineYield 0%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

3-bromo-5-(trifluoromethyl)pyridine (100 mg, 0.44 mmol), methylamine hydrochloride (59.8 mg, 0.88 mmol), and cesium carbonate (490 mg, 1.50 mmol) were suspended in dioxane (3 mL) . The reaction was purged with nitrogen for 30 minutes then 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (7.68 mg, 0.01 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0)-CHLOROFORM ADDUCT (9.16 mg, 8.85 µmol) were added. The reaction was heated to 130 °C in a CEM microwave for 1 hour. No Product formed. Abandoned

Sources & evidence

ORD record
ord-6058a506bcd3404d8683ad593ff991cd
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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