Water → HCID 87146399, compound

HRID 1948733Notes

Reaction equation

HRID 1948733 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].O>C1COCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[C:11](/[CH:12]=[N:21]/[S@@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 87146399HCID 87146399, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-8-methylquinoline-3-carboxaldehyde (2.05 g, 10 mmol) in dry THF (20 mL) under nitrogen was added titanium isopropoxide (5.68 g, 20 mmol) and the mixture stirred at r.t. for 10 minutes. (R)-(+)-2-Methyl-2-propanesulfinamide (1.21 g, 10 mmol) was added to the reaction which was stirred at r.t. for 72 h. Water (20 mL) was added and the mixture was extracted with DCM (150 mL). The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford the title compound as a pale yellow solid (2.4 g, 72%). δH (CDCl3) 9.12 (s, 1H), 8.79 (s, 1H), 7.78 (d, J 8.4 Hz, 1H), 7.67 (d, J 6.8 Hz, 1H), 7.51 (t, J 7.8 Hz, 1H), 2.79 (s, 3H), 1.32 (s, 9H). LCMS (ES+) 309, 311 (M+H)+, RT 3.66 minutes (Method 5).

Workup

  1. stirringwas stirred at r.t. for 72 h
  2. extractionthe mixture was extracted with DCM (150 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1dfafbcf9115462cb7ca848aa205ca79
Source dataset
uspto-grants-2013_03
Patent number
US08399483B2

Reaction notes

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