Water → methyl 5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

HRID 523472Notes

Reaction equation

HRID 523472 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][CH2:23][CH2:24][CH2:25][F:26].O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]([CH2:22][CH2:23][CH2:24][CH2:25][F:26])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 100221-Bromo-4-fluorobutaneHCID 10796Cesium carbonateHCID 84677991methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Product 1

HCID 86698873methyl 5-chloro-1-(4-fluorobutyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 5-chloro-1H-pyrrolo[3,2-b]pyridine-2-carboxylate 11-c (2.9 g, 12.2 mmol) in DMF (50 mL) were added successively cesium carbonate (4 g, 12.2 mmol) and 1-bromo-4-fluorobutane (1.3 mL, 12.2 mmol). The resulting mixture was heated at 60° C. overnight. The reaction mixture was allowed to cool down to room temperature then poured into iced water and the product was extracted 3 times with DCM. The combined organic layers were dried over Na2SO4, filtered and evaporated to give the targeted product 11-d as a yellowish solid. The product was used as such in the next step. m/z=313 (M+H)+, Cl pattern.

Workup

  1. temperatureto cool down to room temperature
  2. extractionthe product was extracted 3 times with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give the targeted product 11-d as a yellowish solid

Sources & evidence

ORD record
ord-3bbaad259d6d4d30ad53f4ca345f1d3c
Source dataset
uspto-grants-2016_05
Patent number
US09339494B2

Reaction notes

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