Potassium Phosphate, Tribasic → 9-[2-(4-fluoro-phenyl)-propenyl]-3,6-dimethyl-6,7,8,9-tetrahydro-5H-1,6,9-triaza-fluorene

HRID 1469503Notes

Reaction equation

HRID 1469503 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[NH:6][C:7]3[CH2:8][CH2:9][N:10]([CH3:15])[CH2:11][C:12]=3[C:13]=2[CH:14]=1.Br[CH:17]=[C:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH3:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1CCC[C@H]1C(O)=O>CN(C=O)C.O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([CH3:19])=[CH:17][N:6]2[C:5]3[N:4]=[CH:3][C:2]([CH3:1])=[CH:14][C:13]=3[C:12]3[CH2:11][N:10]([CH3:15])[CH2:9][CH2:8][C:7]2=3)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 687572963,6-dimethyl-6,7,8,9-tetrahydro-5H-1,6,9-triaza-fluoreneHCID 86644757(1-Bromoprop-1-en-2-yl)-4-fluorobenzene

Product 1

HCID 682836309-[2-(4-fluoro-phenyl)-propenyl]-3,6-dimethyl-6,7,8,9-tetrahydro-5H-1,6,9-triaza-fluorene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a degassed solution of 3,6-dimethyl-6,7,8,9-tetrahydro-5H-1,6,9-triaza-fluorene (201 mg, 1.0 mmol), 1-(2-bromo-1-methyl-vinyl)-4-fluoro-benzene (279 mg, 1.3 mmol), potassium phosphate (530 mg, 2.5 mmol) in DMF (4 mL), L-proline (28 mg, 0.25 mmol) and cuprous iodide (47 mg, 0.25 mmol) were added. The reaction mixture was stirred at 120° C. for 8 h. The reaction mixture was cooled to RT, diluted with water (20 mL) and extracted with EtOAc (4×20 mL). The organic layer was washed with water (5×20 mL), dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by silica gel flash chromatography to yield 9-[2-(4-fluoro-phenyl)-propenyl]-3,6-dimethyl-6,7,8,9-tetrahydro-5H-1,6,9-triaza-fluorene. 1H NMR (CDCl3, freebase) δ (ppm): 8.1 (s, 1H), 7.57 (m, 3H), 7.07 (t, 2H), 6.92 (s, 1H), 3.62 (s, 2H), 2.8 (s, 4H), 2.6 (s, 3H), 2.4 (s, 3H), 2.0 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc (4×20 mL)
  3. washThe organic layer was washed with water (5×20 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customto afford crude material, which
  7. customwas purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-1c43e334df524bfc93d38561f9662969
Source dataset
uspto-grants-2015_04
Patent number
US09006263B2

Reaction notes

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