Cesium carbonate → HCID 86642120, compound

HRID 885911Notes

Reaction equation

HRID 885911 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[N:3]=1.C1(C)C=CC(S(O[CH2:19][CH:20]2[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[O:21]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:19][CH:20]2[CH2:24][O:23][C:22]([CH3:26])([CH3:25])[O:21]2)[N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 1785160256-chloropyridin-2-ol

Product 1

HCID 86642120HCID 86642120, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 2-chloro-6-hydroxypyridine (0.58 g, 4.50 mmol) and 2,2-dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonate (1.29 g, 4.50 mmol) in DMF (10 mL) was added cesium carbonate (2.97 g, 9.00 mmol). The reaction mixture was stirred at 85° C. for 18 h, and then partitioned between EtOAc (50 mL) and water (50 mL). The organic fraction was separated, washed with water (2×50 mL), then brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo to give the title compound (1.03 g, 94%) as an off-white solid that was used without further purification. δH (DMSO-d6) 7.78 (1H, dd, J 8.1 and 7.5 Hz), 7.11 (1H, dd, J 7.5 and 0.6 Hz), 6.86 (1H, dd, J 8.1 and 0.6 Hz), 4.45-4.35 (1H, m), 4.33-4.18 (2H, m), 4.11-4.01 (1H, m), 3.77 (1H, dd, J 8.5 and 6.2 Hz), 1.34 (3H, s), 1.29 (3H, s). LCMS (ES+) 244.1 (M+H)+, RT 3.63 minutes (Method 1).

Workup

  1. custompartitioned between EtOAc (50 mL) and water (50 mL)
  2. customThe organic fraction was separated
  3. washwashed with water (2×50 mL)
  4. dry with materialbrine (50 mL), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b00fb666daa9498b88733e436336d51d
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

Loading…