Isopropyl isocyanate → HCID 59536260, compound

HRID 445312Notes

Reaction equation

HRID 445312 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].[CH:22]([N:25]=[C:26]=[O:27])([CH3:24])[CH3:23]>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:26]([NH:25][CH:22]([CH3:24])[CH3:23])=[O:27])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:9])[F:10]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 59536303HCID 59536303, compound

Product 1

HCID 59536260HCID 59536260, 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 (0.1020 g, 0.345 mmol) in 3 mL of DCM, isopropyl isocyanate (0.0400 mL, 0.407 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) then again with 10-40% EtOAc in hexanes to afford the title compound as a white solid. MS (ESI pos. ion) m/z: 381.1 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 7.48 (t, J=7.75 Hz, 1H) 7.19-7.32 (m, 2H) 7.01-7.14 (m, 2H) 6.55 (s, 1H) 4.30 (s, 1H) 3.98-4.13 (m, 1H) 3.38-3.63 (m, 2H) 2.69-2.98 (m, 2H) 1.13-1.25 (m, 6H).

Workup

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

Sources & evidence

ORD record
ord-f239bfcf7dcc4ef3b31d4fdf68d7a030
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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