4-Fluorophenyl isocyanate → HCID 59536273, compound

HRID 445313Notes

Reaction equation

HRID 445313 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][NH:13]2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[F:22][C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][N:13]2[C:30]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)=[O:31])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 59536303HCID 59536303, compound

Product 1

HCID 59536273HCID 59536273, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-fluoro-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydro-isoquinoline (0.0845 g, 0.286 mmol, Example 71 Step 3) in 3 mL of DCM, 4-fluorophenyl isocyanate (0.0358 mL, 0.315 mmol) was added. The solution was stirred for 1 h. Solvent was evaporated and the residue was purified by silica gel chromatography (0-50% EtOAc in hexanes) to yield the title compound as a white solid. MS (ESI pos. ion) m/z: 433.1 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.51 (t, J=7.75 Hz, 1H) 7.22-7.39 (m, 6H) 7.06-7.19 (m, 2H) 6.96-7.05 (m, 2H) 6.63 (s, 1H) 6.45 (s, 1H) 3.59-3.81 (m, 2H) 2.76-3.08 (m, 2H).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by silica gel chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f79bc7a25c904092956a88ed47f9b51b
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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