2,4-Dichloropyridine → N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amine

HRID 365Notes

Reaction equation

HRID 365 reaction equation
Clc1ccnc(Cl)c1.Nc1ncco1>CC(=O)N(C)C.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>Clc1ccnc(Nc2ncco2)c1

Participants

7

Reactant 2

HCID 335152,4-DichloropyridineHCID 5585212-Aminooxazole

Product 1

HCID 130016260N-(4-chloro-2-pyridinyl)-1,3-oxazol-2-amineYield 1.97%

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 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

oxazol-2-amine (85 mg, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in DMA (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was added and the mixture heated at 100 °C for 70h. The mixture was cooled, filtered and concentrated. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford N-(4-chloropyridin-2-yl)oxazol-2-amine (3.90 mg, 1.967 %).

Sources & evidence

ORD record
ord-1cd8c235ce4f4167a93c6067f176b339
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

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