Potassium Phosphate, Tribasic → HCID 66731996, compound

HRID 1869741Notes

Reaction equation

HRID 1869741 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 2736842Methyl 2-chloropyridine-4-carboxylate

Product 1

HCID 66731996HCID 66731996, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

Methyl 2-chloroisonicotinate (427 mg), 4-(trifluoromethyl)phenylboronic acid (474 mg), potassium phosphate (800 mg), 1,1-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (102 mg), in PhMe (5 ml) were placed in a microwave tube and the contents were heated in the microwave oven for 20 min at 150° C. The cooled mixture was filtered through Hyflo® to remove inorganic material, the Hyflo® was washed with EtOAc and the combined organic extracts were dispersed between H2O and EtOAc. The organic extracts were washed with brine, dried (MgSO4) and evaporated. The crude oil was purified by chromatography on silica using 10-25% EtOAc in hexane to yield the product as a crystalline solid (560 mg, 85%). 1H NMR (400 MHz, CDCl3) δ: 4.01 (3H, s), 7.76 (2H, d, J 8.3), 7.84 (1H, dd, J 1.4, 4.9), 8.18 (2H, d, J 8.2), 8.33 (1H, t, J 1.1), 8.87 (1H, dd, J 0.6, 4.8).

Workup

  1. filtrationThe cooled mixture was filtered through Hyflo®
  2. customto remove inorganic material
  3. washthe Hyflo® was washed with EtOAc
  4. additionthe combined organic extracts were dispersed between H2O and EtOAc
  5. washThe organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe crude oil was purified by chromatography on silica using 10-25% EtOAc in hexane

Sources & evidence

ORD record
ord-8d0c75b27dab4303afb930e2d9cd831c
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

Loading…