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p-Toluenesulfonic acid monohydrate → 1-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 1429896
Notes
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Reaction equation

HRID 1429896 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O.CC1C=CC(S(O)(=O)=O)=CC=1.Cl[C:30]1[C:35]([CH2:36][C:37](O)=[O:38])=[CH:34][CH:33]=[CH:32][N:31]=1>C(O)CCCC>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:14]2[C:30]3=[N:31][CH:32]=[CH:33][CH:34]=[C:35]3[CH2:36][C:37]2=[O:38])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27238314-Benzyloxyaniline hydrochlorideHCID 147395442-(2-Chloropyridin-3-yl)acetic acid

Product 1

HCID 585775191-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneYield 46.9%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(benzyloxy)aniline hydrochloride (2.21 g), 4-methylbenzenesulfonic acid hydrate (0.178 g), and (2-chloropyridin-3-yl)acetic acid (Journal of Medicinal Chemistry, 1990, 33, 2697-2706.) (1.61 g) in 1-pentanol (15 mL) was stirred at 140° C. for 24 h. After cooling to room temperature, the mixture was added to SiO2, and the mixture was concentrated and purified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane) to give 1-[4-(benzyloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one (1.39 g) as a pale yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe mixture was added to SiO2
  3. concentrationthe mixture was concentrated
  4. custompurified by column chromatography (silica gel, eluted with 0%-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-d0e7a35105b4497686d36a8ab93e5ed1
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08940758B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes