tert-Butyl isocyanate → 5-bromo-N-tert-butyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445370Notes

Reaction equation

HRID 445370 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH:7]2[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.[N:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[C:23]=[O:24]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:23]([NH:22][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:24])[CH:7]2[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 595362725-Bromo-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 595364105-bromo-N-tert-butyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round-bottomed flask was added 5-bromo-1-(4-(trifluoromethyl)-phenyl)-1,2,3,4-tetrahydroisoquinoline (44 mg, 124 μmol, from step 3), CH2Cl2 (2 mL), 2-isocyanato-2-methylpropane (12 mg, 124 μmol, Aldrich). The reaction mixture was stirred at RT for 2 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 50% EtOAc/hexanes to give 5-bromo-N-tert-butyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxamide. MS (ESI pos. ion) m/z: 455 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-d8d8434b49e14708a63574c94dc0cf90
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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