Dichloromethane → [6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid ethyl ester

HRID 655264Notes

Reaction equation

HRID 655264 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]3[NH:17][CH:16]=[CH:15][C:12]3=[N:13][CH:14]=2)[CH:6]=[N:5]1.[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Br)[CH3:19].ClCCl>CN(C)C=O>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][N:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([C:7]3[CH:6]=[N:5][N:4]([CH3:3])[CH:8]=3)[CH:10]=2)[CH:15]=[CH:16]1)[CH3:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 687052776-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 68704641[6-(1-Methyl-1H-pyrazol-4-yl)-pyrrolo[3,2-b]pyridin-1-yl]-acetic acid ethyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

In a N2 charged round bottom flask, Sodium Hydride, 60%, (41 mg, 1.01 mmol) was suspended in dimethylformamide (2.5 mL). The solution was maintained under N2 and cooled to 0° C. for 10 minutes. Next, 6-(1-Methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-b]pyridine (200 mg, 1.01 mmol) was dissolved in dimethylformamide (2.5 mL) and added to the cooled solution dropwise. The solution was allowed to stir at 0° C. for an additional 10 minutes. Finally, Bromo-acetic acid ethyl ester (123 uL, 1.11 mmol) was slowly added to the reaction vessel. The reaction was allowed to equilibrate back to room temperature, while stirring for 2 hours. Finally, the solution was transferred to a separatory funnel with dichloromethane (75 mL) and washed with water (2×75 mL). The organic layer was dried over Na2SO4, concentrated down and purified by flash chromatography (0-10% Methanol/dichloromethane step gradient) to afford the title compound (122 mg, 43% yield). MS m/z=285 [M+H+]+

Workup

  1. temperatureThe solution was maintained under N2
  2. additionadded to the cooled solution dropwise
  3. customto equilibrate back to room temperature
  4. stirringwhile stirring for 2 hours
  5. washwashed with water (2×75 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated down
  8. custompurified by flash chromatography (0-10% Methanol/dichloromethane step gradient)

Sources & evidence

ORD record
ord-3da5c835b5b04513bc625b2a801a387f
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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