2-Methoxyethylamine → HCID 18470906, compound

HRID 567817Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[CH3:11][O:12][CH2:13]CN.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([N:37]([CH2:40]C)CC)C.[O:42]1CCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:9]([CH2:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:40]([NH:37][CH2:13][O:12][CH3:11])=[O:42])#[N:10]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(3-Bromophenyl)acetonitrile (40 g, 0.20 mol) was added to a solution of 2-methoxyethylamine (61.3 g, 0.81 mol), triphenylphosphine (8.0 g, 0.03 mol), palladium acetate (4.0 g, 0.01 mol) and triethylamine (62 g, 0.61 mol) in tetrahydrofuran (400 ml). The reaction mixture was heated to 100° C. in a sealed vessel under carbon monoxide @100 psi for 18 hrs, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:pentane (90:10) changing to dichloromethane (100%) and then to dichloromethane:methanol (98:2) to afford the title compound, 14.57 g (33%).

Workup

customafter which time the solvent was removed under reduced pressure
customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:pentane (90:10)

Sources & evidence

ORD record: ord-eea44df6ddee47f3976ed5f7383434cd
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06180627B2

Reaction notes

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