Cesium carbonate → HCID 23582500, compound

HRID 1896501Notes

Reaction equation

HRID 1896501 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[C:13](Cl)[CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].CC1C=C(C)C=C(C)C=1[N+]1CCN(C2C(C)=CC(C)=CC=2C)C=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[NH2:1][C:2]1[C:7]2[C:8]3[CH:14]=[C:13]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[C:5]([C:16]([NH2:18])=[O:17])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 27349171,3-Bis(2,4,6-trimethylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideHCID 23582499HCID 23582499, compound

Product 1

HCID 23582500HCID 23582500, compound

Reagents, catalysts & solvents 2

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

Procedure

A mixture containing 1-amino-8-chloro[1]benzothieno[3,2-c]pyridine-4-carboxamide (Example 1), phenylboronic acid (1.9 equiv), 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride (0.2 equiv), cesium carbonate (2.4 equiv), tris(dibenzylideneacetone)dipalladium (0.1 equiv) in dioxane (0.3 M) was placed in a microwave reactor at 120° C. for 23 min. The resulting mixture was extracted with EtOAc-DMSO and H2O. The organic phase was separated and purified by flash chromatography (EtOAc to 10% MeOH in EtOAc) to provide the title compound.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc-DMSO and H2O
  2. customThe organic phase was separated
  3. custompurified by flash chromatography (EtOAc to 10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-c63862c20e614ea6821405c0cd9d0304
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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