Cesium carbonate → HCID 59383116, compound

HRID 1715175Notes

Reaction equation

HRID 1715175 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:19](=[N:32][C:33]1[S:34][C:35](Br)=[C:36]([CH3:38])[N:37]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O.O1CCOCC1>[C:19](=[N:32][C:33]1[S:34][C:35]([C:7]2[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=2)=[C:36]([CH3:38])[N:37]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 37021224-Acetylphenylboronic acidHCID 59383114HCID 59383114, compound

Product 1

HCID 59383116HCID 59383116, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Acetylphenyl boronic acid (1.8 g, 0.011 mol, 1.1 eq), tetrakistriphenylphosphine palladium(0) (0.7 g, 0.6 mmol), caesium carbonate (9.8 g, 0.03 mol) in water (10 ml), are added to a solution of benzhydrylidene-(5-bromo-4-methyl-thiazol-2-yl)-amine (3.5 g, 0.01 mol) in dioxane (80 ml) and heated at reflux for 6 h. The solvent is removed in vacuo, to yield an oily suspension which is partitioned between DCM (75 ml) and sat. sodium bicarbonate (75 ml). The layers are separated and the organics washed with water (75 ml) and brine (75 ml), dried (MgSO4 and charcoal), filtered and evaporated to a brown solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 h
  3. customThe solvent is removed in vacuo
  4. customto yield an oily suspension which
  5. customis partitioned between DCM (75 ml) and sat. sodium bicarbonate (75 ml)
  6. customThe layers are separated
  7. washthe organics washed with water (75 ml) and brine (75 ml)
  8. dry with materialdried (MgSO4 and charcoal)
  9. filtrationfiltered
  10. customevaporated to a brown solid

Sources & evidence

ORD record
ord-d95e998712b347979e4b605454449330
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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