Sodium Carbonate → HCID 68431886, compound

HRID 889254Notes

Reaction equation

HRID 889254 reaction equation
[K].[CH2:2]([O:9][C:10]1[CH:15]=[C:14](Br)[CH:13]=[C:12]([F:17])[C:11]=1[N:18]1[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:26]B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([CH3:26])[CH:13]=[C:12]([F:17])[C:11]=1[N:18]1[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 139377Methylboronic AcidHCID 68431783HCID 68431783, compound

Product 1

HCID 68431886HCID 68431886, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave vial is added 150 mg (0.33 mmol) of 5-(2-benzyloxy-4-bromo-6-fluorophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt and 125 mg of polystyrene-tetrakis(triphenylphosphine)palladium(0) (0.1 mmol/g) followed by 4.5 mL DME. To this is added 80 mg (1.33 mmole) of methylboronic acid followed by 1.3 mL of a 2.0 M aqueous solution of sodium carbonate. The mixture is heated in a microwave apparatus at 120° C. for 30 min. The resin is filtered and the solvent is removed under reduced pressure. Water is added to the residue and the solution is washed with MTBE. The aqueous phase is used directly in the next step.

Workup

  1. filtrationThe resin is filtered
  2. customthe solvent is removed under reduced pressure
  3. additionWater is added to the residue
  4. washthe solution is washed with MTBE

Sources & evidence

ORD record
ord-4c1bb961fb5344308c21d475c87f8f22
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

Loading…