Methanol → Methyl 1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 749509Notes

Reaction equation

HRID 749509 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7]N=C[C:4]=2[CH:3]=[C:2]1[CH:10]=[O:11].[C-:12]#[N:13].[Na+].[CH3:15][OH:16]>[O-2].[O-2].[Mn+4]>[CH3:15][O:16][C:10]([C:2]1[NH:1][C:9]2[CH:8]=[CH:7][N:13]=[CH:12][C:4]=2[CH:3]=1)=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 8929Sodium CyanideHCID 450795071H-pyrrolo[3,2-c]pyridine-2-carbaldehyde

Product 1

HCID 49759102Methyl 1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

Add to a 0° C. solution of 1H-pyrrolo[3,2-c]pyridine-2-carboxaldehyde (9b-1, 3.24 g, 22.19 mmol) in methanol under argon, sodium cyanide (5.44 g, 111 mmol) and manganese dioxide (9.65 g, 111 mmol). Stir the reaction mixture for 5 h, filter through Celite® and dilute with 500 ml EtOAc. Wash the organic layer with water (2×) and brine, dry over sodium carbonate, filter, and concentrate to provide the title compound (3.27 g) as a pure tan solid. Prepare 1H-pyrrolo[3,2-c]pyridine-2-carboxylic acid amide 6b-1 from 5b-1 by any of the above described procedures for the synthesis compound 6a-1 from ethyl ester 4a-1.

Workup

  1. filtrationfilter through Celite®
  2. additiondilute with 500 ml EtOAc
  3. washWash the organic layer with water (2×) and brine
  4. dry with materialdry over sodium carbonate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-8265ad6bb456489ea8851fc8ab7edb8a
Source dataset
uspto-grants-2008_07
Patent number
US07402672B2

Reaction notes

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