4-Fluorophenyl isocyanate → N-(4-Fluorophenyl)-4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydro-isoquinoline-2(1H)-carboxamide

HRID 445287Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[NH:4][CH2:3]1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>ClCCCl>[F:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([N:4]2[CH2:3][C:2]([CH3:22])([CH3:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]2[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)=[O:32])=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 25-mL round-bottomed flask was charged with 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (118 mg, 0.39 mmol), 4-fluorophenyl isocyanate (43.4 μL, 0.39 mmol) and DCE (5 mL). The reaction mixture was heated at 80° C. for 2 h and the solvent was then removed under vacuum. Purification by silica gel chromatography (20-30% EtOAc in hexanes) provided the title compound as a white solid. MS (ESI, positive ion) m/z: 443 (M+H).

Workup

customthe solvent was then removed under vacuum
customPurification by silica gel chromatography (20-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-03d4bbd4d6944d8f8089cb65b230b7b0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476297B2

Reaction notes

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