Cesium carbonate → HCID 87449702, compound

HRID 390708

Reaction equation

HRID 390708 reaction equation
[CH3:1][C:2]1[S:6][C:5]([NH:7][C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])=[N:4][CH:3]=1.Cl[C:16]1[CH:29]=[C:28]2[C:23](N=CC=C2)=[C:22]2[C:17]=1C=CC=N2.C(=O)([O-])[O-].[Cs+].[Cs+].IC1C=CC=CC=1.[OH-].[NH4+].O>CN1CCCC1=O>[CH3:1][C:2]1[S:6]/[C:5](=[N:7]\[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:9])/[N:4]([C:16]2[CH:29]=[CH:28][CH:23]=[CH:22][CH:17]=2)[CH:3]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 778655-Chloro-1,10-phenanthrolineHCID 47197229HCID 47197229, compoundHCID 86589665Water ammonium hydroxide

Product 1

HCID 87449702HCID 87449702, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

To a 4 mL vial equipped with a septum cap and stir bar was added N-(5-methyl-1,3-thiazol-2-yl)pyrrolidine-1-carboxamide (21 mg, 0.1 mmol), copper(I) trifluoromethanesulfonate benzene complex (10 mg, 0.02 mmol), 5-chloro-1,10-phenanthroline (8.5 mg, 0.04 mmol) and cesium carbonate (38.9 mg, 0.12 mmol). The mixture was placed under a nitrogen atmosphere. Iodobenzene (0.12 mmol) in 1-methyl-2-pyrrolidinone (1.0 mL) was added to the mixture. The reaction mixture was heated at 120° C. for overnight. A solution of concentrated ammonium hydroxide/water (1:2, 1 mL) was added and the mixture was filtered and solvent removed under reduced pressure. The residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid).

Workup

  1. customTo a 4 mL vial equipped with a septum
  2. customcap
  3. filtrationthe mixture was filtered
  4. customsolvent removed under reduced pressure
  5. customThe residue was purified by reverse phase HPLC (C8, gradient 10-100% acetonitrile/water/0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-b9a1c7ad96754a8e8302465963d697d4
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Linked notes

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