Cesium carbonate → HCID 67086875, compound

HRID 1477736Notes

Reaction equation

HRID 1477736 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10](I)[CH:9]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[N:19]1>CN(C=O)C>[Cl:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[C:10]([N:19]2[N:20]=[CH:21][CH:22]=[N:18]2)[CH:9]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1394524-Chloro-2-iodobenzoic acidHCID 178418936HCID 178418936, compound

Product 1

HCID 67086875HCID 67086875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cs2CO3 (12.0 g, 37 mmol) was added portionwise to a rt solution of commercially available 4-chloro-2-iodobenzoic acid (5.22 g, 18.5 mmol) in DMF (25 mL) followed by 1H-1,2,3-triazole (1.61 mL, 27.8 mmol) and Cu(I)I (210 mg, 1.1 mmol). The resulting blue suspension was stirred at 120° C. for 30 min, then the rxn mixture was quenched with 2M aq. HCl and filtered through a celite plug before being extracted with DCM (3×). The combined org. layers were dried (Na2SO4), filtered and evaporated in vacuo to give the crude product that was purified by FC (Biotage SP1: eluting with DCM/MeOH 95:5+0.1% AcOH) to give the title compound A-1-1 as a brown solid. LC-MS A: tR=0.66 min; [M(35Cl)+H]+=224.10.

Workup

  1. customthe rxn mixture was quenched with 2M aq. HCl
  2. filtrationfiltered through a celite plug
  3. extractionbefore being extracted with DCM (3×)
  4. dry with materiallayers were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product that
  8. customwas purified by FC (Biotage SP1: eluting with DCM/MeOH 95:5+0.1% AcOH)

Sources & evidence

ORD record
ord-f0c7c3026e1b4b85a151651bd650214c
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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