Sodium Carbonate → HCID 66864112, compound

HRID 2093084Notes

Reaction equation

HRID 2093084 reaction equation
Cl[C:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][C:3]=1[CH:18]=O.C([O-])([O-])=O.[Na+].[Na+].Cl.[NH:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28].[C:33](O[K])(C)(C)[CH3:34]>CS(C)=O.CN(C=O)C>[CH3:28][N:27]1[C:2]2[CH2:7][CH2:6][N:5]([S:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3)(=[O:9])=[O:10])[CH2:4][C:3]=2[CH:18]=[C:29]1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 86650192HCID 86650192, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 66864112HCID 66864112, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 4-chloro-1-[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carbaldehyde (1 eq) obtained in step II of example 200 in DMSO was added Na2CO3(4.0 eq) and sarcosine hydrochloride (2.0 eq) at room temp and the reaction mixture was stirred for 1.5 hr at 40° C. Reaction mass was then quenched with water and extracted with ethyl acetate. Organic layer was separated and dried over anhydrous Na2SO4, concentrated under reduced pressure to afford crude product, which, was dissolve in DMF and added to the mixture of tBuOK (1.0 eq) in DMF at 0° C. and stirred at room temperature for 2 h Reaction mass was quenched in water and extracted with ethyl acetate. Organic layer was separated dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded ethyl 1-methyl-5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate.

Workup

  1. customReaction mass
  2. customwas then quenched with water
  3. extractionextracted with ethyl acetate
  4. customOrganic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. stirringstirred at room temperature for 2 h
  9. customReaction mass
  10. customwas quenched in water
  11. extractionextracted with ethyl acetate
  12. customOrganic layer was separated
  13. dry with materialdried over anhydrous Na2SO4
  14. concentrationconcentrated under reduced pressure
  15. customto afford crude product, which
  16. customon purification by column chromatography

Sources & evidence

ORD record
ord-4bb5a2a8700444b2aa1416464c4ad695
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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