Dimethylformamide → 4-(4-(Chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridine

HRID 2098913Notes

Reaction equation

HRID 2098913 reaction equation
[CH3:1][C:2]1([CH3:24])[C:6]([C:7]2[CH:8]=[C:9]([CH2:22]O)[CH:10]=[CH:11][C:12]=2[C:13]2[C:18]([F:19])=[CH:17][N:16]=[C:15]([O:20][CH3:21])[CH:14]=2)=[CH:5][CH2:4][CH2:3]1.CN(C=O)C.S(Cl)([Cl:32])=O>C(Cl)Cl>[Cl:32][CH2:22][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[C:18]([F:19])=[CH:17][N:16]=[C:15]([O:20][CH3:21])[CH:14]=2)=[C:7]([C:6]2[C:2]([CH3:24])([CH3:1])[CH2:3][CH2:4][CH:5]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57467619(3-(5,5-Dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanol

Product 1

HCID 574676204-(4-(Chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-(5,5-dimethylcyclopent-1-enyl)-4-(5-fluoro-2-methoxypyridin-4-yl)phenyl)methanol T8.3 (34.5 mg, 105 μmol) was added DCM (1.1 mL) and DMF (8.2 μL, 105 μmol) followed by thionyl chloride (15 μL, 211 μmol) in an ice bath. The reaction was then stirred at room temperature for 1 hour. The reaction was concentrated and directly purified on silica gel to afford 4-(4-(chloromethyl)-2-(5,5-dimethylcyclopent-1-enyl)phenyl)-5-fluoro-2-methoxypyridine T8 (36 mg) as an oil (99%).

Workup

  1. concentrationThe reaction was concentrated
  2. customdirectly purified on silica gel

Sources & evidence

ORD record
ord-7e766e8f11bb42fcae5724dc331d9540
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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