Dimethyl Sulfoxide → HCID 60869526, compound

HRID 1396021Notes

Reaction equation

HRID 1396021 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[C:9]1([CH:16]=[CH:15][CH:14]=[C:12]([OH:13])[CH:11]=1)[OH:10].CS(C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:9]2[CH:11]=[C:12]([OH:13])[CH:14]=[CH:15][CH:16]=2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 5054ResorcinolHCID 10796Cesium carbonateHCID 3458175-Chloro-2-fluoropyridine

Product 1

HCID 60869526HCID 60869526, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution consisting of 5-chloro-2-fluoropyridine (1.3 mL, 13 mmol) and resorcinol (2.1 g, 19 mmol) and DMSO (30 mL) was added Cs2CO3 (6.3 g, 19 mmol). The reaction vessel was heated at 40° C. for 22 hours then diluted with CH2Cl2 (60 mL) and washed with saturated aq. NH4Cl (100 mL). The organic layer was dried (MgSO4) and concentrated. The crude residue was purified (FCC) to give the title compound (1.0 g, 37%). MS (ESI+): calcd. for C11H8ClNO2, 221.02. m/z found, 222.1 (M+H)+. 1H NMR (CDCl3): 8.14 (d, J=2.6 Hz, 1H), 7.65 (dd, J=8.7, 2.7 Hz, 1H), 7.26-7.22 (m, 1H), 6.89 (dd, J=8.7, 0.5 Hz, 1H), 6.69-6.65 (m, 2H), 6.60 (t, J=2.3 Hz, 1H).

Workup

  1. washwashed with saturated aq. NH4Cl (100 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-85052ddc43bd436db8cd77b1e8c68cdd
Source dataset
uspto-grants-2014_12
Patent number
US08901111B2

Reaction notes

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