Ethyl Acetate → HCID 89408388, compound

HRID 516204Notes

Reaction equation

HRID 516204 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](/[CH:8]=[N:9]/[S@](C(C)(C)C)=O)[C:3]=1[F:16].CC([S@](N)=O)(C)C.Cl[C:25]1[CH:30]=[CH:29]N=[C:27]([CH:31]=[O:32])[C:26]=1F.[C:34]([O-:37])([O-])=O.[Cs+].[Cs+].[CH3:40][CH2:41][O:42]C(C)=O>C(Cl)Cl>[C:31]1([O:32][C:34](=[O:37])[NH:9][C@H:8]([C:4]2[C:3]([F:16])=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=2)[CH2:40][CH:41]=[O:42])[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 5

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 722127674-Chloro-3-fluoropyridine-2-carbaldehydeHCID 90199529HCID 90199529, compound

Product 1

HCID 89408388HCID 89408388, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S,E)-N-((4-Chloro-3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide: A solution of (R)-2-methylpropane-2-sulfinamide (0.540 g, 4.32 mmol), 4-chloro-3-fluoropicolinaldehyde (0.627 g, 3.93 mmol) and Cs2CO3 (1.921 g, 5.89 mmol) in DCM (20 mL) was stirred for 1 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to provide the desired product (1.1 g, 100%). MS (ESI) m/z: 263.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-ef915f9a6d9b4044bb7866b93f1d3405
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

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