Allyl bromide → HCID 19977722, compound

HRID 864916Notes

Reaction equation

HRID 864916 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH2:25]>O1CCCC1>[CH2:25]([O:1][N:2]1[C:10]2[C:5](=[N:6][C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:4]=[CH:3]1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 19958191HCID 19958191, compound

Product 1

HCID 19977722HCID 19977722, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl 1-hydroxypyrrolo[3,2-b]pyridine-5,6-dicarboxylate (6.2 g, 0.022 mol) is dissolved in (200 mL) dry tetrahydrofuran and cooled to 0° C. under nitrogen. Sodium hydride (0.77 g, 0.033 mol) is added in portions over ten minutes and the reaction is stirred for 30 minutes at 0° C. Allyl bromide (2.01 mL, 0.024 mol) is added all at once to the suspension and the mixture allowed to warm to room temperature and then stirred for 16 hours. The mixture is filtered and the filtrate concentrated in vacuo. The resulting oil is chromatographed using 4:1 hexanes/ethyl acetate and then increasing the polarity to 2:1 hexanes/ethyl acetate to give the product as a yellow oil in 89% yield.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 16 hours
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe resulting oil is chromatographed
  6. temperatureincreasing the polarity to 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-b29f9ee75ea44a839189fa38833576a6
Source dataset
uspto-grants-1996_10
Patent number
US05565411

Reaction notes

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