Potassium Phosphate, Tribasic → HCID 90030834, compound

HRID 1488119Notes

Reaction equation

HRID 1488119 reaction equation
I[C:2]1[NH:6][C:5]([C:7]#[N:8])=[N:4][CH:3]=1.[CH3:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1B1OC(C)(C)C(C)(C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.COCCOC>[C:7]([C:5]1[NH:6][C:2]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:10]=2[CH3:9])[C:14]([O:16][CH3:17])=[O:15])=[CH:3][N:4]=1)#[N:8]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 532171365-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester2×HCID 67984831HCID 67984831, compound2×

Product 1

HCID 90030834HCID 90030834, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Into a 100-mL three neck round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 5-iodo-1H-imidazole-2-carbonitrile (compound 234.2, 700 mg, 3.20 mmol) in a solvent mixture of DME and H2O (30/3 mL). Methyl 4-methyl-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 1.06 g, 3.84 mmol), K3PO4 (2.71 g, 12.8 mmol), Xphos (152 mg, 0.32 mmol), Pd(PPh3)4 (369 mg, 0.32 mmol) were added to the reaction. The reaction mixture was stirred overnight at 90° C., then concentrated under reduced pressure. The residue was diluted with 50 mL of ethyl acetate, then was washed with 3×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent to furnish 160 mg (21%) of the title compound as a white solid.

Workup

  1. customInto a 100-mL three neck round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with 50 mL of ethyl acetate
  5. washwas washed with 3×20 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by a silica gel chromatography with ethyl acetate/petroleum ether (1/2) as eluent

Sources & evidence

ORD record
ord-f424101011d840c4a1345eb61ed87861
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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