Cesium carbonate → HCID 86296390, compound

HRID 1773670Notes

Reaction equation

HRID 1773670 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][N:21]1[C:25](B(O)O)=[C:24]([CH3:29])[CH:23]=[N:22]1.C([O-])([O-])=O.[Cs+].[Cs+]>ICCC.COCCOC.O>[CH3:20][N:21]1[C:25]([C:16]2[C:10]3[N:11]([CH3:15])[C:12](=[O:14])[NH:13][C:9]=3[CH:8]=[C:7]([C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH3:19])[CH:17]=2)=[C:24]([CH3:29])[CH:23]=[N:22]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 72218278B-(1,4-Dimethyl-1H-pyrazol-5-yl)boronic acidHCID 117601430HCID 117601430, compound

Product 1

HCID 86296390HCID 86296390, 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.) was added 1,4-dimethyl-1H-pyrazol-5-ylboronic acid (72 mg, 0.32 mmol, 3 equiv.), Cs2CO3 (141 mg, 0.43 mmol, 4 equiv.) and PEPPSI™-IPr catalyst (8 mg, 0.02 mmol, 0.1 equiv.) and dissolved in 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. After cooling, the reaction was extracted with EtOAc and washed with water and saturated NH4C1. After drying with MgSO4, it was filtered and concentrated to dryness. Purification was carried out by reverse phase HPLC to furnish 7-(1,4-dimethyl-1H-pyrazol-5-yl)-5-(3,5-dimethylisoxazol-4-yl)-1-methyl-1H-benzo[d]imidazol-2(3H)-one.

Workup

  1. temperatureAfter cooling
  2. extractionthe reaction was extracted with EtOAc
  3. washwashed with water and saturated NH4C1
  4. dry with materialAfter drying with MgSO4, it
  5. filtrationwas filtered
  6. concentrationconcentrated to dryness
  7. customPurification

Sources & evidence

ORD record
ord-c0a2a5398fb747e1ad912f657420f093
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

Loading…