Water → HCID 68754457, compound

HRID 624154Notes

Reaction equation

HRID 624154 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)=[C:2]=[O:3].[CH2:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][NH:14]1.O>ClCCl>[CH3:15][C:16]1([CH3:17])[C:21]([CH3:13])([CH3:20])[O:12][B:10]([C:7]2[CH:6]=[CH:5][C:4]([NH:1][C:2]([N:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:13]3)=[O:3])=[CH:9][CH:8]=2)[O:11]1

Participants

5

Reactant 3

HCID 962WaterHCID 422478IsoindolineHCID 57416338(4-Isocyanatophenyl)boronic acid

Product 1

HCID 68754457HCID 68754457, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

500 mg (4-Isocyanatophenyl)boronic acid pinacolester (1.979 mmol) and 365 mg isoindoline (2.97 mmol) were dissolved in 10 ml dichloromethane and the resultant mixture was stirred over night at room temperature. After adding water, the mixture was extracted several times with dichloromethane, the combined organic phases were washed with dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. Column chromatography of the residue with dichloromethane resulted in the title compound.

Workup

  1. extractionthe mixture was extracted several times with dichloromethane
  2. washthe combined organic phases were washed
  3. dry with materialwith dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7530678d204e42f88e0f0a936c3c32da
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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