2-(Chloromethyl)-6-fluoroquinoline → HCID 67592265, compound

HRID 610368

Reaction equation

HRID 610368 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C@H:8]2[C@@H:17]([OH:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14](O)[CH:15]=3)[O:10][CH2:9]2)=[CH:5][CH:4]=1.[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28](CCl)[CH:27]=[CH:26]2>C(Cl)Cl>[F:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28]([C:14]1[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C@@H:8]([O:7][C:6]1[CH:20]=[CH:21][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C@H:17]3[OH:18])[CH:27]=[CH:26]2

Participants

4

Reactant 2

HCID 112410072-(Chloromethyl)-6-fluoroquinolineHCID 67825695HCID 67825695, compound

Product 1

HCID 67592265HCID 67592265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the method of Example 13, using flash chromatography with 35:1 CH2Cl2 :isopropanol as eluant and recrystallization from CH2Cl2 for purification of the product, the title product of Example 20 (0.20 g, 0.69 mmol) and 6-fluoro-2-chloromethylquinoline were converted to present title product, 0.104 g (34%), m.p. 151-153.5° C. MS calculated: 447.1486, found: 447.1494.

Workup

  1. customisopropanol as eluant and recrystallization from CH2Cl2
  2. customfor purification of the product

Sources & evidence

ORD record
ord-0f141ec7a9f34689a502e2b2857106e7
Source dataset
uspto-grants-1999_12
Patent number
US05998451

Linked notes

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