tert-Butylsulfinamide, (R)-(+)- → HCID 87146059, compound

HRID 1627504Notes

Reaction equation

HRID 1627504 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=O)=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][C:16]([S@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>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](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 120991792-Chloro-7-fluoroquinoline-3-carbaldehyde

Product 1

HCID 87146059HCID 87146059, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-7-fluoroquinoline-3-carboxaldehyde (6.3 g, 30 mmol) in dry THF (200 mL) under nitrogen was added titanium(IV) isopropoxide (17.0 g, 60 mmol) and the reaction mixture stirred at r.t. for 10 minutes. (R)-(−)-2-Methyl-2-propane-sulfinamide (3.6 g, 30 mmol) was added to the reaction mixture, which was stirred at r.t. for 72 h and partitioned between water (20 mL) and DCM (150 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the title compound (7.2 g, 76%) as a pale yellow solid. δH (CDCl3) 9.09 (1H, s), 8.83 (1H, s), 7.96 (1H, dd, J=6.0 Hz), 7.69 (1H, d, J=7.2 Hz), 7.42 (1H, t, J=8.4 Hz), 1.32 (9H, s).

Workup

  1. stirringwas stirred at r.t. for 72 h
  2. custompartitioned between water (20 mL) and DCM (150 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fddf48d80f8449bdb059f7da1caf18b0
Source dataset
uspto-grants-2014_07
Patent number
US08785628B2

Reaction notes

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