Cesium carbonate → HCID 59401365, compound

HRID 2060887Notes

Reaction equation

HRID 2060887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[OH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[O:23])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]=[O:23])=[CH:14][CH:13]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1455253-Chloro-4-fluorobenzonitrileHCID 3442904-Hydroxy-1-naphthaldehyde

Product 1

HCID 59401365HCID 59401365, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-chloro-4-fluorobenzonitrile (1.09 g, 7.00 mmol) in DMSO (25 mL) was added 4-hydroxy-1-napthaldehyde (1.20 g, 7.0 mmol) and caesium carbonate (4.55 g, 14.0 mmol). The reaction mixture was heated to 80° C. for 24 h. After cooling to rt the mixture was partitioned between EtOAc (40 mL) and saturated NaHCO3 (50 mL), and the aqueous phase washed with EtOAc (50 mL). Solvent was removed in vacuo and the residue purified by column chromatography (EtOAc:isohexane, 2:8) to give the title compound: RT=4.10 min; m/z (ES+)=NO IONISATION [M+H]+. δH(DMSO) 7.10 (1H, t), 7.46 (1H, d), 7.78 (1H, t), 7.88 (1H, t), 7.94 (1H, d), 8.19 (1H, d), 8.32 (1H, d), 8.37 (1H, d), 9.28 (1H, d), 10.33 (1H, s).

Workup

  1. temperatureAfter cooling to rt the mixture
  2. customwas partitioned between EtOAc (40 mL) and saturated NaHCO3 (50 mL)
  3. washthe aqueous phase washed with EtOAc (50 mL)
  4. customSolvent was removed in vacuo
  5. customthe residue purified by column chromatography (EtOAc:isohexane, 2:8)

Sources & evidence

ORD record
ord-4e7330065cb84529a84b4dbd833031b5
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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