4-Fluorophenyl isocyanate → 1-(3,4-Difluorophenyl)-N-(4-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445309Notes

Reaction equation

HRID 445309 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:6][C:7]=1[F:8].[F:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[C:27]=[O:28])=[CH:22][CH:21]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)=[O:28])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 59536265HCID 59536265, compound

Product 1

HCID 595364251-(3,4-Difluorophenyl)-N-(4-fluorophenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3,4-difluorophenyl)-1,2,3,4-tetrahydroisoquinoline (0.1019 g, 0.415 mmol) in 3 mL of DCM, 4-fluorophenyl isocyanate (0.0550 mL, 0.484 mmol) was added. The clear solution was stirred for 1 h. The solvent was evaporated and residue was taken into small amount of DCM. The resulting precipitate was collected to yield the title compound as a white solid. The filtrate was concentrated and purified by silica gel chromatography (0-30% EtOAc in hexanes) to afford another batch of the title compound as a white solid. MS (ESI pos. ion) m/z: 383 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.16-7.37 (m, 6H) 6.93-7.13 (m, 5H) 6.54 (s, 1H) 6.40 (s, 1H) 3.66 (t, J=6.28 Hz, 2H) 2.77-3.08 (m, 2H).

Workup

  1. customThe solvent was evaporated
  2. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-97f326aab9224c4cb8ef81e2114519eb
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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