Potassium Phosphate, Tribasic → HCID 66832605, compound

HRID 1914513Notes

Reaction equation

HRID 1914513 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[N:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.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>[N:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:2]2[N:7]=[C:6]([CH2:8][N:9]3[C:17](=[O:18])[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:10]3=[O:19])[CH:5]=[C:4]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[N:3]=2)[CH:31]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 86663709HCID 86663709, compound

Product 1

HCID 66832605HCID 66832605, compoundYield 33.2%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-ylmethyl]-isoindole-1,3-dione (0.30 g, 0.72 mmol) in DME (4 mL) and H2O (1 mL) was added 3-pyridine boronic acid (0.09 g, 0.72), Pd(PPh3)4 (0.04 g, 0.04 mmol), and K3PO4 (0.21 g, 1.01 mmol) at rt. The resulting mixture was heated to 80° C. for 12 hours then allowed to cool to rt. At which time the mixture was partitioned between H2O (5 mL) and EtOAc (5 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2×5 mL). The organic layers were combined, dried over Na2SO4, filtered, concentrated and purified by FCC to afford the title compound as a colorless solid (0.11 g, 33%). MS (ESI): mass calcd. for C25H15F3N4O2, 460.1; m/z found, 461.2 [M+H]+.

Workup

  1. temperatureto cool to rt
  2. customAt which time the mixture was partitioned between H2O (5 mL) and EtOAc (5 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (2×5 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by FCC

Sources & evidence

ORD record
ord-9e5ba5bdd8e746a6930aef41a10f3cd2
Source dataset
uspto-grants-2013_12
Patent number
US08614201B2

Reaction notes

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