HCID 15838063, compound → HCID 15838056, compound

HRID 1901584Notes

Reaction equation

HRID 1901584 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[C:16]3[CH:17]=[C:18]([F:27])[CH:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]=3[N:14]=[CH:13]1)[C:6]([CH3:28])=[C:5]2[C:29]([O:31]C)=[O:30].BrC1C(C)=C(C(OC)=O)C2C(=CC=C(F)C=2)N=1>C(O)CCC>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[C:16]3[CH:17]=[C:18]([F:27])[CH:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:15]=3[N:14]=[CH:13]1)[C:6]([CH3:28])=[C:5]2[C:29]([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 15838063HCID 15838063, compoundHCID 23368198HCID 23368198, compound

Product 1

HCID 15838056HCID 15838056, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Methyl 6-fluoro-3-methyl-2-(6-fluoro-4-phenyl-1-benzimidazolyl)quinoline-4-carboxylate: A mixture of 2-bromo-4-carbomethoxy-6-fluoro-3-methylquinoline, obtained in Example 1D, (2.53 g, 8.48 mmol) and the product of example 68C (1.80 g, 8.48 mmol) in n-butanol (12 mL) was heated at reflux for 18 h. The reaction was allowed to cool to room temperature and solvent was removed. The residue was chromatographed (1:1 hexanes-ethyl acetate) to provide the desired product (0.135 g, 0.31 mmol) in 3.7% yield as a tan solid, mp=208°-210° C.; NMR(CDCl3): 8.27 (s, 1H), 8.13 (dd, 1H), 8.01 (d, 2H), 7.41-7.62 (m, 5H), 7.30 (dd, 1H), 7.06 (dd, 1H), 4.16 (s, 3H), 2.40 (s, 3H); IR(KBr): 1734; Mass spectrum: m/z 430.0 (M+H).

Workup

  1. customobtained in Example 1D, (2.53 g, 8.48 mmol)
  2. temperatureat reflux for 18 h
  3. customsolvent was removed
  4. customThe residue was chromatographed (1:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-0e4036247ee64b4eb94ed1645e07ce4b
Source dataset
uspto-grants-1996_11
Patent number
US05578609

Reaction notes

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