4-Fluorophenyl isocyanate → N-(4-fluorophenyl)-1-(6-(trifluoromethyl)-pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445385Notes

Reaction equation

HRID 445385 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>C(Cl)Cl>[F:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([N:10]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]2[C:6]2[CH:7]=[N:8][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:4][CH:5]=2)=[O:30])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 595362781-(6-(Trifluoromethyl)pyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536388N-(4-fluorophenyl)-1-(6-(trifluoromethyl)-pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude 1-(6-(trifluoromethyl)pyridin-3-yl)-1,2,3,4-tetrahydroisoquinoline was dissolved in CH2Cl2 (1.0 mL) and 1-fluoro-4-isocyanatobenzene (32 μL, 273 μmol) was added. The reaction was stirred 17 h under N2 at RT. The reaction was directly purified by HPLC to give N-(4-fluorophenyl)-1-(6-(trifluoromethyl)-pyridin-3-yl)-3,4-dihydroisoquinoline-2(1H)-carboxamide as a white solid. MS (ESI pos. ion) m/z: 416 (M+1).

Workup

  1. customThe reaction was directly purified by HPLC

Sources & evidence

ORD record
ord-7da499076e954ad59569eb163f747e7b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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