Cesium carbonate → HCID 58223427, compound

HRID 41282Notes

Reaction equation

HRID 41282 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.Br[C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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:29]3[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=3)=[C:16]2[S:17][CH:18]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 122863-BromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67095627HCID 67095627, compound

Product 1

HCID 58223427HCID 58223427, compoundYield 38.7%

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 3-bromopyridine (33.9 mg, 0.215 mmol), cesium carbonate (99.1 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 eight 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 60%) to obtain the title compound (32.4 mg, 0.0692 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-21daddd0f3d94c418e542eb1f8d04d55
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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