4-Fluorophenyl isocyanate → HCID 57326212, compound

HRID 445298Notes

Reaction equation

HRID 445298 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)[NH:7][CH2:6][CH2:5]2.C(N(C(C)C)CC)(C)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([N:38]=[C:39]=[O:40])=[CH:34][CH:33]=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:21])[F:20])=[CH:14][CH:13]=1)[N:7]([C:39]([NH:38][C:35]1[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=1)=[O:40])[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 709554-Fluorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 59536348HCID 59536348, compound

Product 1

HCID 57326212HCID 57326212, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-fluoro-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (0.3 g, 1.0 mmol) and diisopropylethylamine (0.2 mL, 0.919 mmol) in anhydrous dichloromethane (6 mL) was treated with 4-fluorophenyl isocyanate (0.14 g, 1.0 mmol) and stirred at RT for 16 h. Formation of a white precipitate was observed which was collected by filtration. The solid was dried under high vacuum to give 6-fluoro-N-(4-fluorophenyl)-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide (0.35 g, 80%). MS (ESI pos. ion) m/z: 433 (M+H).

Workup

  1. filtrationwas collected by filtration
  2. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-514bfbe7396c4321ae22592a454c040d
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

Loading…