Dimethylformamide → HCID 21192923, compound

HRID 1067289Notes

Reaction equation

Br[C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH2:21][C:22](OC)([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=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+].[CH3:35][Sn](C)(C)C.CN(C)[CH:42]=[O:43]>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>[CH3:35][C:2]1[C:3]([NH:18][C:19](=[O:32])[C:20]2[CH:25]=[CH:24][C:23]([O:43][CH3:42])=[C:22]([C:26]([F:28])([F:29])[F:27])[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

Participants

Conditions

Temperature: 100 °C

Procedure

N-(8-Bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-3-methoxy-3-trifluoromethylbenzamide (0.25 g), was combined with lithium chloride (0.06 g), tetramethyltin (0.08 ml) and bis(triphenylphosphine)palladium(II)chloride (0.025 g) in dimethylformamide (5 ml) and the mixture warmed to 100° C. for 24 h. Solvent was removed at reduced pressure, filtered (Celite pad) and the filtrate column chromatographed (silica gel, diethyl ether eluant) to give N-(8-methyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinolin-7-yl)-4methoxy-3-trifluoromethylbenzamide (0.16 g).

Workup

customSolvent was removed at reduced pressure
filtrationfiltered (Celite pad)
customthe filtrate column chromatographed (silica gel, diethyl ether eluant)

Sources & evidence

ORD record: ord-9a4ef05fc6454c108aed72a616c47854
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248754B1

Reaction notes

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