tert-Butylsulfinamide, (R)-(+)- → HCID 87146907, compound

HRID 242142Notes

Reaction equation

HRID 242142 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C1COCC1>[Cl:1][C:2]1[C:11](/[CH:12]=[N:22]/[S@@:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 866626352-Chloro-7-fluoro-8-methylquinoline-3-carbaldehyde

Product 1

HCID 87146907HCID 87146907, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described for Intermediate 1, 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (6.6 g, 29.5 mmol), titanium(IV) isopropoxide (17.0 g, 60 mmol), (R)-2-methyl-2-propanesulfinamide (3.6 g, 29.5 mmol) and THF (200 mL) gave the title compound (8.3 g, 86%) as a yellow solid. δH (CDCl3) 9.12 (1H, s), 8.73 (1H, s), 7.71 (1H, dd, J 6.0 Hz), 7.40 (1H, t, J 8.2 Hz), 2.69 (3H, s), 1.32 (9H, s).

Sources & evidence

ORD record
ord-223e6c94f44843b4bea164218e6fae4e
Source dataset
uspto-grants-2014_02
Patent number
US08653105B2

Reaction notes

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