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(2-Aminothiophen-3-yl)(phenyl)methanone → Cyclopropyl-(6-methyl-4-phenyl-thieno[2,3-b]pyridin-5-yl)-methanone

HRID 133528
Notes
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Reaction equation

HRID 133528 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[CH:15]1([C:18](=[O:23])[CH2:19][C:20](=O)[CH3:21])[CH2:17][CH2:16]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:15]1([C:18]([C:19]2[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]3[CH:5]=[CH:4][S:3][C:2]3=[N:1][C:20]=2[CH3:21])=[O:23])[CH2:17][CH2:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 644720(2-Aminothiophen-3-yl)(phenyl)methanoneHCID 110188691-Cyclopropyl-butane-1,3-dione

Product 1

HCID 11514843Cyclopropyl-(6-methyl-4-phenyl-thieno[2,3-b]pyridin-5-yl)-methanoneYield 8.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 60 mg (0.29 mmol) (2-amino-thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 20) in 2 ml acetic acid was added 50 mg (0.39 mmol) of 1-cyclopropyl-butane-1,3-dione and one drop of sulfuric acid. The mixture was then stirred at 100° C. for 10 minutes in a microwave and then concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 6:1) afforded 7 mg (8%) cyclopropyl-(6-methyl-4-phenyl-thieno[2,3-b]pyridin-5-yl)-methanone as a colorless oil. ES-MS m/e (%): 294 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f8697feb0854967a8b7977ce8ccc7c8
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07390903B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes