Diethyl benzylphosphonate → HCID 67021244, compound

HRID 735480Notes

Reaction equation

HRID 735480 reaction equation
C(OP([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)OCC)C.[H-].[Na+].[Cl:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][N:24]2[C:32]([C:33]3[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=3)[CH:36]=O)=[C:31]3[C:26]([C:27]([C:41]([F:44])([F:43])[F:42])=[CH:28][CH:29]=[CH:30]3)=[N:25]2)=[C:21]([F:47])[CH:20]=1>CN1C(=O)N(C)CCC1.C(O)C.[Pt]=O>[Cl:18][C:19]1[CH:46]=[CH:45][C:22]([CH2:23][N:24]2[C:32]([C:33]3[CH:40]=[CH:39][CH:38]=[C:35]([CH2:36][CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH:34]=3)=[C:31]3[C:26]([C:27]([C:41]([F:44])([F:43])[F:42])=[CH:28][CH:29]=[CH:30]3)=[N:25]2)=[C:21]([F:47])[CH:20]=1

Participants

7

Reactant 3

HCID 14122Diethyl benzylphosphonateHCID 24758Sodium hydrideHCID 86603029HCID 86603029, compound

Product 1

HCID 67021244HCID 67021244, compound

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a suspension of benzyl-phosphonic acid diethyl ester (20 μL, 1 eq) and sodium hydride (6 mg, 1.5 eq) in DMPU (0.5 mL), 3-[2-(4-chloro-2-fluoro-benzyl)-7-trifluoromethyl-2H-indazol-3-yl]-benzaldehyde (45 mg, 1 eq) was added. The reaction mixture was stirred for 45 minutes at room temperature, quenched with water and extracted with diethyl ether. The volatiles were removed and the residue purified by flash chromatography (silica, ethyl acetate/n-heptane, 2:8). The product obtained was dissolved in ethanol (2 mL) and hydrogenated at 1 atm using 7% platinum oxide as a catalyst. Filtration through Celite® and flash chromatography, eluent: dichloromethane/n-hepatane, 1:1, furnished the title compound in 11% overall yleld.

Workup

  1. additionwas added
  2. customquenched with water
  3. extractionextracted with diethyl ether
  4. customThe volatiles were removed
  5. customthe residue purified by flash chromatography (silica, ethyl acetate/n-heptane, 2:8)
  6. customThe product obtained
  7. filtrationFiltration through Celite® and flash chromatography, eluent

Sources & evidence

ORD record
ord-d672aaa82f93490e86eeaac4a0231ca2
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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