Sodium Bicarbonate → 1-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine

HRID 23546Notes

Reaction equation

HRID 23546 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:28])=[CH:16][C:17]([N:18]3[CH2:27][CH2:26][C:21]4(OCC[O:22]4)[CH2:20][CH2:19]3)=[C:12]2[C:11]([CH3:29])=[C:10]1[CH3:30].C(=O)([O-])O.[Na+]>Cl.O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:28])=[CH:16][C:17]([N:18]3[CH2:27][CH2:26][C:21](=[O:22])[CH2:20][CH2:19]3)=[C:12]2[C:11]([CH3:29])=[C:10]1[CH3:30]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 12134654HCID 12134654, compound

Product 1

HCID 121346551-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridineYield 81.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

After 1-(2,4-dichlorophenyl)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]-pyridine (5.21 g) was stirred in a mixture of 4 M hydrochloric acid (60 mL) and tetrahydrofuran (60 mL) at room temperature for 2.5 hours, 6 M hydrochloric acid (30 mL) was added thereto and the resulting mixture was stirred overnight. After completion of the reaction, the reaction mixture was poured into a saturated aqueous sodium hydrogen-carbonate solution and extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, after which the desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The crystals thus obtained were washed with ethyl acetate to obtain 1-(2,4-dichlorophenyl)-4-(4-oxopiperidin-1-yl)-2,3,6-trimethyl-1H-pyrrolo[2,3-b]pyridine (3.83 g).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationafter which the desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crystals thus obtained
  7. washwere washed with ethyl acetate

Sources & evidence

ORD record
ord-caac4ca01fad401d8a0672d766d57787
Source dataset
uspto-grants-2005_02
Patent number
US06852732B2

Reaction notes

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