Thionyl Chloride → HCID 86303959, compound

HRID 2271475Notes

Reaction equation

HRID 2271475 reaction equation
Cl[CH:2]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]([O:9][CH3:10])=[N:7][CH:8]=1.ClC1C=C(C2C=C(C(C3C=CC(F)=CC=3)O)[CH:35]=[N:36]C=2OC)C=CC=1.S(Cl)(Cl)=O>C(Cl)Cl>[Cl:17][C:13]1[CH:12]=[C:11]([C:5]2[CH:4]=[C:3]([CH:2]([NH:36][CH3:35])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH:8]=[N:7][C:6]=2[O:9][CH3:10])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 86303956HCID 86303956, compoundHCID 90415043HCID 90415043, compound

Product 1

HCID 86303959HCID 86303959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(Chloro(4-fluorophenyl)methyl)-3-(3-chlorophenyl)-2-methoxypyridine. To a cooled solution, 0° C., of [5-(3-chlorophenyl)-6-methoxypyridin-3-yl](4-fluorophenyl)methanol (Example 14, 1.43 g, 4.17 mmol), in DCM (10 mL), was added thionyl chloride (744 mg, 6.25 mmol) dropwise. The solution was allowed to warm up to room temperature, and stirred for 1 h. The reaction mixture was concentrated under reduced pressure. Purification (FCC, SiO2, 0-10% EtOAc/hexanes) afforded the title compound, which was used directly for the next step.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customPurification (FCC, SiO2, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ec8733f530304afeaa0001253c283d1c
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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