methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate → (1H-pyrrolo[2,3-b]pyridin-2-yl)methanol

HRID 1777737Notes

Reaction equation

HRID 1777737 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](OC)=[O:11].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 17390026methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 53273992(1H-pyrrolo[2,3-b]pyridin-2-yl)methanolYield 39.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (300 mg) in THF (4.5 mL) was added LiAlH4 (1.7 mL, 1M in THF). The ice bath was removed and the reaction mixture was stirred at RT for 2 h. LiAlH4 (2.8 mL, 1M in THF) was added and the stirring was pursued for 20 h at RT. DCM and 1M NaOH were added and the phases were separated. The org. layer was dried (Na2SO4) and evaporated in vacuo to afford 100 mg of oil. LC-MS (B): tR=0.34 min; [M+H]+: 149.28.

Workup

  1. customThe ice bath was removed
  2. additionLiAlH4 (2.8 mL, 1M in THF) was added
  3. waitthe stirring was pursued for 20 h at RT
  4. additionDCM and 1M NaOH were added
  5. customthe phases were separated
  6. dry with materiallayer was dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-75b0c74bfd5345bdb73bf20130527542
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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