Cesium carbonate → HCID 67317949, compound

HRID 1013693Notes

Reaction equation

HRID 1013693 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:23][N:22]=1>CC(O)(C)C>[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH2:6][NH:7][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[N:23][N:22]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2721091-Chloro-4-phenylphthalazineHCID 30843432,4-Dimethoxybenzylamine hydrochloride

Product 1

HCID 67317949HCID 67317949, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

In a nitrogen purged 75 mL sealed tube, dissolved 2,4-dimethoxybenzylamine hydrochloride (2.54 g, 12.5 mmol), cesium carbonate (4.06 g, 12.5 mmol) in tBuOH (15 mL). Added 1-chloro-4-phenylphthalazine (2.0 g, 8.31 mmol)and the tube was stirred at 100° C. for 17 h. The tube was cooled to RT, and the mixture was concentrated in vacuo. Dissolved the crude material in DCM, and filtered the solution to remove cesium carbonate. Performed silica gel chromatography using 0-100% EtOAc/Hex and concentrated to yield N-(2,4-dimethoxybenzyl)-4-phenylphthalazin-1-amine as orange oil. MS [M+H]=372; Calc'd 371.4 for C23H21N3O2.

Workup

  1. customIn a nitrogen purged 75 mL
  2. customsealed tube
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionDissolved the crude material in DCM
  5. filtrationfiltered the solution
  6. customto remove cesium carbonate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a8067941d7e04be0bb5611fc6fa3a7b6
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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