HCID 15817177, compound → HCID 9887116, compound

HRID 1901583Notes

Reaction equation

HRID 1901583 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:20]3[C:15](=[C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]1)[C:6]([CH3:27])=[C:5]2[C:28]([O:30]C)=[O:29].BrC1C(C)=C(C(OC)=O)C2C(=CC=C(F)C=2)N=1>C(O)C>[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:20]3[C:15](=[C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]1)[C:6]([CH3:27])=[C:5]2[C:28]([OH:30])=[O:29]

Participants

4

Reactant 2

HCID 15817177HCID 15817177, compoundHCID 15838063HCID 15838063, compound

Product 1

HCID 9887116HCID 9887116, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 6-fluoro-3-methyl-2-(4-phenyl-1-indolinyl)quinoline-4-carboxylate: A mixture of 2-bromo-4-carbomethoxy-6-fluoro-3-methylquinoline, obtained in step 1D, (5.96 g, 20.00 mmol), and the product of step 1H (3.90 g, 20.00 mmol) in absolute ethanol (100 mL) was stirred at reflux for 65 h. The mixture was allowed to cool to room temperature and the solid filtered to provide the desired product (6.64 g, 16.09 mmol) in 80.4% yield as a yellow solid, mp=213°-215° C.; NMR(CDCl3): 6.52-7.93 (m, 11H), 4.18 (t, 2H), 4.10 (s, 3H), 3.23 (t, 2H), 2.45 (s, 3H); IR(KBr): 2860, 1728; Mass spectrum: m/z 413.1 (M+H).

Workup

  1. customobtained in step 1D, (5.96 g, 20.00 mmol),
  2. temperatureat reflux for 65 h
  3. filtrationthe solid filtered

Sources & evidence

ORD record
ord-415086b8f1134ba48da574bdb3cf7ea1
Source dataset
uspto-grants-1996_11
Patent number
US05578609

Reaction notes

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