tert-Butylsulfinamide, (R)-(+)- → HCID 87146580, compound

HRID 1627510Notes

Reaction equation

HRID 1627510 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[C:8]([CH:13]=O)=[CH:7]2.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([Cl:12])[C:8](/[CH:13]=[N:21]/[S@@:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])=[CH:7]2

Participants

4

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 35767472HCID 35767472, compound

Product 1

HCID 87146580HCID 87146580, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

Following the procedure described for Intermediate 1, 8-bromo-2-chloro-quinoline-3-carbaldehyde (280 mg, 1.04 mmol), (R)-(+)-2-methyl-2-propanesulfinamide (125 mg, 1.04 mmol) and titanium isopropoxide (0.61 mL, 2.08 mmol) afforded the title compound (335 mg, 87%) as a yellow solid. δH (CDCl3) 9.12 (1H, s), 8.82 (1H, s), 8.15 (1H, dd, J 7.52, 1.31 Hz), 7.92 (1H, dd, J 8.17, 1.30 Hz), 7.52-7.44 (1H, m), 1.33 (9H, s).

Sources & evidence

ORD record
ord-6aa7c17b08404a419431b162d859e2ae
Source dataset
uspto-grants-2014_07
Patent number
US08785628B2

Reaction notes

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