Trimethyl phosphite → HCID 86584825, compound

HRID 1835345Notes

Reaction equation

HRID 1835345 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.[CH3:34][O:35][C:36]([C:38]1[CH:43]=[CH:42][C:41](B(O)O)=[CH:40][CH:39]=1)=[O:37].P([O-])([O-])([O-])=O.[K+].[K+].[K+].P(OC)(OC)OC>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:34][O:35][C:36](=[O:37])[C:38]1[CH:43]=[CH:42][C:41]([C:12]2[CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH3:21])[C:9]([C:8](=[O:23])[N:7]([CH2:6][C:5]3[CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:27]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:25]=3)[CH3:24])=[CH:10][N:11]=2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 8472Trimethyl phosphiteHCID 62657Potassium Phosphate, TribasicHCID 27343694-Methoxycarbonylphenylboronic acidHCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 86584825HCID 86584825, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 200 mg (0.346 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4), 95 mg (0.52 mmol) 4-methoxycarbonylphenylboronic acid and 155 mg (0.692 mmol) potassium phosphate in 4 ml dioxane was deoxygenated by three freeze-thaw cycles. After addition of 9.5 mg (0.010 mmol) tris(dibenzylideneacetone)dipalladium(0) and 0.0025 ml (0.02 mmol) trimethyl phosphite the reaction mixture was stirred at 95° C. for 5 h. Cooling to room temperature was followed by dilution with tert-butyl methyl ether, filtration over Decalite and evaporation of the solvent in vacuo. Column chromatography afforded 50 mg (25%) of the title compound as a light brown solid.

Workup

  1. customwas deoxygenated by three freeze-thaw cycles
  2. temperatureCooling to room temperature
  3. filtrationwas followed by dilution with tert-butyl methyl ether, filtration over Decalite and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-a9410b3b745a4af88a9a0d3e96b5f12c
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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