1,3-Dibromopropane → HCID 66728202, compound

HRID 573304Notes

Reaction equation

HRID 573304 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[NH:13][CH:12]=2)=[CH:7][CH:6]=1.[H-].[Na+].[Br:22][CH2:23][CH2:24][CH2:25]Br>O>[Br:22][CH2:23][CH2:24][CH2:25][N:13]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[C:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=2)=[CH:12]1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 66727950HCID 66727950, compound

Product 1

HCID 66728202HCID 66728202, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3-[4-(methoxymethoxy)phenyl]-1H-pyrrolo[3,2-b]pyridine (650 mg) was added NaH (60% in oil, 153 mg) at 0° C. After stirring at room temperature for 1 h, the mixture was added dropwise to 1,3-dibromopropane (0.778 mL). The mixture was stirred at room temperature for 2 h. The mixture was added to water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (486 mg).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-d97080c5c41d47ec802dc3dd8b860d90
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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