1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(3-chloro-4-fluoro-phenyl)-7,8-dimethoxy-5-methyl4H-1,3,4-triaza-phenalene

HRID 1351213Notes

Reaction equation

HRID 1351213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:20]([CH2:21]I)[CH2:19][C:18]3[C:23]4[C:10]2=[N:11][CH:12]=[N:13][C:14]=4[CH:15]=[C:16]([O:26][CH3:27])[C:17]=3[O:24][CH3:25])[CH:5]=[CH:6][C:7]=1[F:8].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:20]([CH3:21])=[CH:19][C:18]3[C:23]4[C:10]2=[N:11][CH:12]=[N:13][C:14]=4[CH:15]=[C:16]([O:26][CH3:27])[C:17]=3[O:24][CH3:25])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 114434104-(3-chloro-4-fluoro-phenyl)-5-iodomethyl-7,8-dimethoxy-5,6-dihydro-4H-1,3,4-triaza-phenalene

Product 1

HCID 210983894-(3-chloro-4-fluoro-phenyl)-7,8-dimethoxy-5-methyl4H-1,3,4-triaza-phenalene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(3-chloro-4-fluoro-phenyl)-5-iodomethyl-7,8-dimethoxy-5,6-dihydro-4H-1,3,4-triaza-phenalene (0.125 g, 0.25 mmol) (from Example 18, Step F, supra) in toluene (25 mL) was added DBU (0.37 mL, 2.5 mmol) (Fluka). The reaction mixture was heated at 120° C. for 1 hours. The mixture was then diluted with chloroform (100 mL) and washed with H2O. The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (3:1:0.05) as eluent to give the desired 4-(3-chloro-4-fluoro-phenyl)-7,8-dimethoxy-5-methyl-4H-1,3,4-triaza-phenalene as a white solid. (Yield 0.093 g, 100%).

Workup

  1. washwashed with H2O
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-d5ef27165d1e431daef99258aaeb82c6
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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