Cesium carbonate → HCID 86296391, compound

HRID 1773716Notes

Reaction equation

HRID 1773716 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16](I)[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:19])[O:4][N:3]=1.[CH3:20][C:21]1[C:25](B2OC(C)(C)C(C)(C)O2)=[C:24]([CH3:35])[O:23][N:22]=1.C([O-])([O-])=O.[Cs+].[Cs+]>ICCC.COCCOC.O>[CH3:1][C:2]1[C:6]([C:7]2[CH:17]=[C:16]([C:25]3[C:21]([CH3:20])=[N:22][O:23][C:24]=3[CH3:35])[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=2)=[C:5]([CH3:19])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol esterHCID 117601430HCID 117601430, compound

Product 1

HCID 86296391HCID 86296391, compound

Reagents, catalysts & solvents 2

HCID 336431-IodopropaneCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

To a microwave vial containing 5-(3,5-dimethylisoxazol-4-yl)-7-iodo-1-methyl-1H-benzo[d]imidazol-2(3H)-one (40 mg, 0.11 mmol, 1 equiv.) were added 3,5-dimethylisoxazole-4-boronic acid pinacol ester (72 mg, 0.32 mmol, 3 equiv.), Cs2CO3 (141 mg, 0.43 mmol, 4 equiv.), PEPPSI™-IPr catalyst (8 mg, 0.02 mmol, 0.1 equiv.) and DME-H2O (20 mL, 0.2 M, 2/1, v/v). The mixture was heated to 140° C. After 1 hr, the reaction was complete. Following cooling, the reaction mixture was extracted with EtOAc and the organic solution was washed with water, saturated NH4Cl. After drying with MgSO4, it was filtered and concentrated to dryness. The resulting solid was washed with EtOAc. Purification of the residue was carried out by reverse phase HPLC to furnish the title compound.

Workup

  1. temperatureFollowing cooling
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washthe organic solution was washed with water, saturated NH4Cl
  4. dry with materialAfter drying with MgSO4, it
  5. filtrationwas filtered
  6. concentrationconcentrated to dryness
  7. washThe resulting solid was washed with EtOAc
  8. customPurification of the residue

Sources & evidence

ORD record
ord-1f11ee8e2ce249f9986bb2e6ad791d7c
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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