Cesium carbonate → HCID 86296390, compound

HRID 1773715Notes

Reaction equation

HRID 1773715 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.) were 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 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 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 under reduced pressure. Purification of the residue was carried out by reverse phase HPLC to furnish the desired product.

Workup

  1. temperatureFollowing cooling
  2. extractionthe reaction 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 under reduced pressure
  7. customPurification of the residue

Sources & evidence

ORD record
ord-2b3c171c094a40a28e1ce988e7a23ed9
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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