Potassium Phosphate, Tribasic → HCID 58223465, compound

HRID 41280Notes

Reaction equation

HRID 41280 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:15]2[N:21]=[C:20]([O:22][CH3:23])[C:19]([NH:24][CH2:25][CH2:26][CH3:27])=[C:16]2[S:17][CH:18]=1.Cl.Cl[C:30]1[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=1.CC(C)([O-])C.[Na+].[O-]P([O-])([O-])=O.[K+].[K+].[K+].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>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].O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:15]2[N:21]=[C:20]([O:22][CH3:23])[C:19]([N:24]([CH2:25][CH2:26][CH3:27])[C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)=[C:16]2[S:17][CH:18]=1

Participants

9

Reactant 5

HCID 62657Potassium Phosphate, TribasicHCID 818524-Chloropyridine hydrochlorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxideHCID 67095627HCID 67095627, compound

Product 1

HCID 58223465HCID 58223465, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a 1,4-dioxane (0.7 mL) solution of 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-N-propylpyrazolo[5,1-b][1,3]thiazole-7-amine (70 mg, 0.179 mmol) were added 4-chloropyridine hydrochloride (32.2 mg, 0.215 mmol), sodium tert-butoxide (20.6 mg, 0.215 mmol), potassium phosphate tribasic (64.6 mg, 0.304 mmol), tris(dibenzylideneacetone)dipalladium (8.2 mg, 0.009 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (7.77 mg, 0.0134 mmol), and the mixture was stirred at 100° C. for seven hours. After the reaction mixture was returned to room temperature, water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate, and the solvent was distilled off under reduced pressure. The residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate: 10% then 80%) to obtain the title compound (49.4 mg, 0.105 mmol).

Workup

  1. customwas returned to room temperature
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by medium pressure amino silica gel column chromatography (n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-b92e23db1b844069afc76f0c138d76b9
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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