Sodium hydride → HCID 66966841, compound

HRID 1435882Notes

Reaction equation

HRID 1435882 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]2[NH:9][C:10]([C:12]([O:14]C)=O)=[CH:11][C:4]=12.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[NH4+].[Cl-]>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(C)=O>[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10]3[N:9]([C:5]=2[N:6]=[CH:7][CH:8]=1)[CH2:19][CH2:20][CH:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:12]3=[O:14]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76300Ethyl 4-bromobutyrateHCID 37818560Methyl 4-(methylsulfanyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 66966841HCID 66966841, compound

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Step 4 (0.35 g, 1.6 mmol) in DMF (20 mL) at 0° C. was added NaH (1.2 eq.). After a period of 5 min., were added nBu4NI (0.10 g) and ethyl 4-bromobutyrate (0.40 mL). After a period of 1 h at room temperature, the reaction mixture was poured over saturated NH4Cl and EtOAc. The organic phase was separated, washed with H2O and dried over NaSO4. After evaporation the crude product was purified by flash chromatography. The bis ester was then dissolved in THF (7.0 mL) and a 1.06 M of THF solution of potassium tert-butoxide (2.2 mL) was added at 0° C. After a period of 1 h at room temperature, the reaction mixture was then poured over saturated NH4Cl and EtOAc. The organic phase was separated, dried over Na2SO4 and evaporated under reduced pressure to provide the title compound as a mixture of ethyl and methyl ester.

Workup

  1. waitAfter a period of 1 h at room temperature
  2. customThe organic phase was separated
  3. washwashed with H2O
  4. dry with materialdried over NaSO4
  5. customAfter evaporation the crude product
  6. customwas purified by flash chromatography
  7. dissolutionThe bis ester was then dissolved in THF (7.0 mL)
  8. additiona 1.06 M of THF solution of potassium tert-butoxide (2.2 mL) was added at 0° C
  9. waitAfter a period of 1 h at room temperature
  10. additionthe reaction mixture was then poured over saturated NH4Cl and EtOAc
  11. customThe organic phase was separated
  12. dry with materialdried over Na2SO4
  13. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-968f0cdf3ed048599bb56bec2743e027
Source dataset
uspto-grants-2009_11
Patent number
US07618979B2

Reaction notes

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