Potassium Phosphate, Tribasic → HCID 67960629, compound

HRID 1505386Notes

Reaction equation

HRID 1505386 reaction equation
I[C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:28][C:29]1(C)[C:33](C)(C)OB(C(C)=C)O1>CN(C=O)C.O>[CH3:33][C:29]([C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])=[CH2:28]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 67236776HCID 67236776, compound2×

Product 1

HCID 67960629HCID 67960629, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-iodo-4-[(5-nitro-2-pyridinyl)oxy]benzonitrile (Intermediate 129, 5.0 g) in DMF (50 mL) were added K3PO4 (5.77 g, 27.24 mmol), Pd(tBu3)2 (696 mg, 1.36 mmol) and 4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane (3.84 mL, 20.43 mmol) and the reaction mixture was stirred for 4 hours at 110° C. After cooling the reaction was diluted with water (100 mL) and extracted with ethyl acetate (3×100 mL). The organic layer was washed with ice cold brine (3×50 mL), dried (Na2SO4), filtered and evaporated and the residue was purified by flash chromatography on silica gel (SNAP 100 g) eluting from 100:0 to 80:20 cyclohexane/ethyl acetate to afford the title compound (1.8 g) as white solid.

Workup

  1. temperatureAfter cooling the reaction
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe organic layer was washed with ice cold brine (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography on silica gel (SNAP 100 g)
  8. washeluting from 100:0 to 80:20 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-105b955b757d4fb18767e6c1cd24d7dd
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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