Sodium bis(2-methoxyethoxy)aluminiumhydride → 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

HRID 1618508Notes

Reaction equation

HRID 1618508 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][C:9](=O)[C:8]([CH3:13])([CH3:12])[C:5]2=[N:6][CH:7]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][CH2:9][C:8]([CH3:13])([CH3:12])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 669587906-Bromo-3,3-dimethyl-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one

Product 1

HCID 672849816-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Prepared according to procedure K using 6-bromo-3,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-2(3H)-one (300 mg, 1.244 mmol), sodium bis(2-methoxyethoxy)-aluminium hydride (1.131 mL, 3.73 mmol) in toluene (3 mL). After purification 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine was obtained as a white solid.

Workup

  1. customPrepared
  2. customAfter purification 6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine
  3. customwas obtained as a white solid

Sources & evidence

ORD record
ord-9777ed74a7dd43c4bca7b6b4ce060dc0
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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