2-Methoxyethylamine → Methyl 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylate

HRID 337595Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:54]1[CH:55]=[C:56]([C:64]([O:66][CH3:67])=[O:65])[C:57]2[C:62]([CH:63]=1)=[CH:61][CH:60]=[CH:59][CH:58]=2.[CH3:68][O:69][CH2:70][CH2:71][NH2:72]>C1(C)C=CC=CC=1.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:68][O:69][CH2:70][CH2:71][NH:72][C:54]1[CH:55]=[C:56]([C:64]([O:66][CH3:67])=[O:65])[C:57]2[C:62]([CH:63]=1)=[CH:61][CH:60]=[CH:59][CH:58]=2

Participants

Conditions

Temperature: 100 °C

Procedure

Freshly purified cesium carbonate (1.4 eq.), palladium(II) acetate (0.02 eq.) and rac-BINAP (0.03 eq.) were combined in anhydrous toluene (0.25 M). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, methyl 3-bromo-1-naphthalenecarboxylate (1 eq.) and 2-methoxyethylamine (1.2 eq.) were added and the resulting mixture was heated at 100° C. for 20 h. The now black suspension was cooled to RT, diluted with ether and filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a brown oil that can be purified further by way of column chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) to afford the title compound as a yellow oil.

Workup

customThe vessel was repeatedly evacuated
additionback-filled with nitrogen
temperatureThe now black suspension was cooled to RT
filtrationfiltered through a pad of celite
customConcentration of the filtrate in vacuo afforded a brown oil that
customcan be purified further by way of column chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record: ord-713959d0e52f4649834d6ee39b1f38af
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889714B2

Reaction notes

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