Sodium borohydride → 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropan-1-ol

HRID 1753069Notes

Reaction equation

HRID 1753069 reaction equation
[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([CH3:17])([CH3:16])[C:12](OC)=[O:13])[CH:3]=1.[BH4-].[Na+]>CCO>[I:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([CH3:17])([CH3:16])[CH2:12][OH:13])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90094007methyl 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanoate

Product 1

HCID 900938832-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropan-1-olYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 2-(3-iodo-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanoate (Preparation 67, 10.8 g, 31.38 mmol) in EtOH (100 mL) was added sodium borohydride (2.37 g, 62.8 mmol) and the reaction stirred at room temperature for 5 hours. The reaction was quenched by the addition of water (100 mL) and the phases separated through a phase separation cartridge. The organic layer was concentrated in vacuo to afford and orange oil that was triturated with ether to afford an orange solid as the title compound (3.86 g, 39%).

Workup

  1. customThe reaction was quenched by the addition of water (100 mL)
  2. customthe phases separated through a phase separation cartridge
  3. concentrationThe organic layer was concentrated in vacuo
  4. customto afford
  5. customorange oil that was triturated with ether

Sources & evidence

ORD record
ord-a8a52fafde3c43c385db4245911574f3
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

Loading…