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1-Cyclopropyl-butane-1,3-dione → Cyclopropyl-(6-methyl-2,4-diphenyl-thieno[2,3-b]pyridin-5-yl)-methanone

HRID 133549
Notes
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Reaction equation

HRID 133549 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[CH:21]1([C:24](=[O:29])[CH2:25][C:26](=O)[CH3:27])[CH2:23][CH2:22]1>C(O)(=O)C.S(=O)(=O)(O)O>[CH:21]1([C:24]([C:25]2[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]3[CH:5]=[C:4]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[S:3][C:2]3=[N:1][C:26]=2[CH3:27])=[O:29])[CH2:23][CH2:22]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 110188691-Cyclopropyl-butane-1,3-dioneHCID 28325476(2-Amino-5-phenyl-thiophen-3-yl)-phenyl-methanone

Product 1

HCID 11624869Cyclopropyl-(6-methyl-2,4-diphenyl-thieno[2,3-b]pyridin-5-yl)-methanoneYield 17%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic Acid
Solvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 0.130 g (0.465 mmol) (2-amino-5-phenyl-thiophen-3-yl)-phenyl-methanone in 7 ml acetic acid was added 62 mg (0.491 mmol) of 1-cyclopropyl-butane-1,3-dione and one drop of sulfuric acid. The mixture was then stirred at 110° C. for 20 minutes in a microwave and then concentrated in vacuo. Preparative HPLC (30% CH3CN/H20) afforded 29 mg (17%) cyclopropyl-(6-methyl-2,4-diphenyl-thieno[2,3-b]pyridin-5-yl)-methanone as a light yellow powder. ES-MS m/e (%): 370 (M+H+, 100).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e0fce0ffee6444d5a759b9313063c088
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