Benzyl Alcohol → benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

HRID 1696218Notes

Reaction equation

HRID 1696218 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][CH:12]=[CH:13][C:3]=12.[C:14]1([CH2:20]O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC.O>CN(C)C=O>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:9])=[CH:6][N:5]=[C:4]2[NH:11][CH:12]=[CH:13][C:3]=12

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 260764404-Chloro-1H-pyrrolo(2,3-b)pyridine-5-carboxylic acid

Product 1

HCID 57928592benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-Carboxylic acid (343 mg) in N,N-dimethylformamide (4 ml) was added phenylmethanol (375 μl) 4-dimethylaminopyridine (428 mg) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (676 mg). After stirring at ambient temperature for 3 days, the reaction mixture was poured into water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with chloroform to give benzyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (200 mg) as a yellow powder.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with chloroform

Sources & evidence

ORD record
ord-d5c699157a6d4a7dacb2efe8f337fa7d
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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