2-Methoxyethylamine → HCID 18470906, compound

HRID 2228743Notes

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-4a590a3bf7dd4ad09fa3ec8340a1698c
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417203B1

Reaction notes

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