Tetraethyltin → HCID 21192929, compound

HRID 1067294Notes

Reaction equation

Br[C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH2:8][CH2:7]2.[Cl-].[Li+].[CH2:35]([Sn](CC)(CC)CC)[CH3:36]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:35]([C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=2)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9]([C:12](=[O:17])[C:13]([F:15])([F:14])[F:16])[CH2:8][CH2:7]2)[CH3:36]

Participants

Conditions

Temperature: 120 °C

Procedure

N-(8-Bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxy-3-trifluoromethylbenzamide (0.525 g), lithium chloride (0.127 g), tetraethyltin (0.47 g) and bis(triphenylphosphine)palladium(II)chloride (0.04 g) were combined in dimethylformamide (10 ml) and the mixture stirred under argon at 120° C. for 20 h. Solvent as removed at reduced pressure, the residue dissolved in dichloromethane and filtered through Celite. Solvent was removed at reduced pressure and the residue column chromatographed (silica gel, ethyl acetate/hexane mixtures) to give the title compound (0.18 g) as an oil.

Workup

customSolvent as removed at reduced pressure
dissolutionthe residue dissolved in dichloromethane
filtrationfiltered through Celite
customSolvent was removed at reduced pressure
customthe residue column chromatographed (silica gel, ethyl acetate/hexane mixtures)

Sources & evidence

ORD record: ord-c994ae9ca0ea4ae895c2b51d32fca5f8
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248754B1

Reaction notes

Loading…