Sodium Hydroxide → HCID 68484005, compound

HRID 2381149Notes

Reaction equation

HRID 2381149 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:14]([O:16]C)=[O:15].[OH-].[Na+:24]>CO>[F:1][C:2]1[CH:21]=[C:20]([I:22])[CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[C:6]1[C:14]([O-:16])=[O:15].[Na+:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59452205HCID 59452205, compound

Product 1

HCID 68484005HCID 68484005, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.46 g, 1.09 mmol) in methanol (4 ml) was added 1M aqueous solution of sodium hydroxide (1.4 ml, 1.40 mmol) and the reaction was heated at reflux for 1.5 hours. The reaction mixture was concentrated in vacuo and azeotroped with toluene (15 ml), methanol (15 ml), toluene (15 ml) and dichloromethane to afford the crude title compound as a waxy white solid (0.50 g, quantitative yield). LCMS (method B): RT=2.11 min, (M−H)−=395; M+H+=397.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customazeotroped with toluene (15 ml), methanol (15 ml), toluene (15 ml) and dichloromethane

Sources & evidence

ORD record
ord-c33e88bf7408446e876f5a12f43c3d09
Source dataset
uspto-grants-2012_09
Patent number
US08258152B2

Reaction notes

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