Potassium Phosphate, Tribasic → HCID 16752714, compound

HRID 911759Notes

Reaction equation

HRID 911759 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[N:19]=[C:20]([NH2:23])[S:21][CH:22]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:17][C:18]1[N:19]=[C:20]([NH:23][C:2]2[C:7]([O:8][C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[CH:6][CH:5]=[CH:4][N:3]=2)[S:21][CH:22]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 741432-Amino-4-methylthiazoleHCID 86631466HCID 86631466, compound

Product 1

HCID 16752714HCID 16752714, compoundYield 47.5%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A 50 mLround bottom flask was charged with 2-(2-chloropyridin-3-yloxy)benzonitrile (0.667 g, 2.89 mmol), 4-methylthiazol-2-amine (0.300 g, 2.63 mmol), potassium phosphate (0.614 g, 2.89 mmol) and toluene (7 mL). The reaction mixture was degassed with nitrogen. Tris(dibenzylideneacetone)-dipalladium (0) (0.0602 g, 0.0657 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.0418 g, 0.0723 mmol) were added, and the reaction mixture was degassed with nitrogen. The reaction mixture was warmed to 90° C. and degassed water (2 mL) was added. The reaction mixture was stirred at 90° C. overnight. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using 10-40% ethyl acetate in hexanes as eluent to afford the title compound as a yellow solid (0.385 g, 46.6% yield). 1H NMR (CDCl3) δ 8.19 (dd, 1H), 7.68 (dd, 1H), 7.49 (m, 1H), 7.19 (dd, 1H), 7.15 (dd, 1H), 6.85 (m, 2H), 6.39 (m, 1H), 2.29 (d, 3H); Mass spectrum (esi) m/z=309 (100).

Workup

  1. customThe reaction mixture was degassed with nitrogen
  2. customthe reaction mixture was degassed with nitrogen
  3. customdegassed water (2 mL)
  4. additionwas added
  5. additionWater was added
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-29f57729417947c8b3890e7111508713
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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