Cesium carbonate → (NE,R)-N-[(2-chloro-3-fluoro-4-pyridinyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1396322Notes

Reaction equation

HRID 1396322 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH:7]=[CH:8][N:9]=1)[CH:5]=O.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][C:18]([S@:21]([NH2:23])=[O:22])([CH3:20])[CH3:19]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[C:3]([F:10])=[C:4](/[CH:5]=[N:23]/[S@@:21]([C:18]([CH3:20])([CH3:19])[CH3:17])=[O:22])[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27631602-Chloro-3-fluoro-4-formylpyridineHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 90199456(NE,R)-N-[(2-chloro-3-fluoro-4-pyridinyl)methylidene]-2-methylpropane-2-sulfinamideYield 91.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 2-chloro-3-fluoroisonicotinaldehyde (0.75 g, 4.70 mmol) and Cs2CO3 (2.297 g, 7.05 mmol) in DCM (20 mL) was added a solution of (R)-2-methylpropane-2-sulfinamide (0.570 g, 4.70 mmol) in DCM (20 mL) dropwise for 10 min. The solution was then stirred for 3.5 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo to give (R,E)-N-((2-chloro-3-fluoropyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide (1.13 g, 91%) as a yellow oil which solidified upon standing. MS (ESI) m/z: 263.0 (M+H)+.

Workup

  1. washwashed with brine (3×20 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84b7f8f35b324a458ffe447207acebea
Source dataset
uspto-grants-2014_12
Patent number
US08901115B2

Reaction notes

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