Tetrahydrofuran → HCID 68431651, compound

HRID 889253Notes

Reaction equation

HRID 889253 reaction equation
[K:1].[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.CO[CH2:28][CH2:29]OC.[C:32](=O)([O-])[O-].[Na+].[Na+].[CH2:38]1[CH2:42]O[CH2:40][CH2:39]1>>[K:1].[CH2:32]([C:14]1[CH:13]=[C:12]([F:17])[C:11]([N:18]2[S:22](=[O:24])(=[O:23])[NH:21][C:20](=[O:25])[CH2:19]2)=[C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:15]=1)[C:29]1[CH:28]=[CH:42][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 68431783HCID 68431783, compound

Product 1

HCID 68431651HCID 68431651, compound

Conditions

Temperature
100 °C

Procedure

To a microwave vial is added 90 mg (0.199 mmole) of 5-(2-benzyloxy-4-bromo-6-fluorophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one potassium salt (intermediate from 1) and 60 mg of polystyrene-tetrakis(triphenylphosphine)palladium(0) (0.1 mmol/g) followed by 4.5 mL DME. To this is added 84 mg (0.396 mmole) of benzyl-9-BBN (0.78 mL of a 1.0 M solution in THF) followed by 84 mg (0.79 mmol) of sodium carbonate (0.39 mL of a 2.0 M aqueous solution). The mixture is heated in a microwave apparatus at 100° C. for 10 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-4cd2b47068dc4663be82e261a92e37f2
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

Loading…