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1,10-Phenanthroline → N-(7-methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-yl)-benzamide

HRID 917462
Notes
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Reaction equation

HRID 917462 reaction equation
[C:1]([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH3:20])=[CH:17][N:16]=[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:14]=1I)=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.O1CCCC1.[Cu]I>[CH3:20][O:19][C:18]1[C:13]2[N:12]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][C:14]=2[C:15]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 589626981-Benzoyl-3-(3-iodo-5-methoxy-2-phenyl-pyridin-4-yl)-thiourea

Product 1

HCID 11653416N-(7-methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-yl)-benzamideYield 81.2%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 1140TolueneSolvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
130 °C

Procedure

A stirred suspension of 600 mg (1.23 mmol) 1-benzoyl-3-(3-iodo-5-methoxy-2-phenyl-pyridin-4-yl)-thiourea, 23 mg (0.12 mmol)-copper(I) iodide, 44 mg (0.25 mmol) 1,10-phenanthroline and 799 mg (2.45 mmol) cesium carbonate in 4 ml toluene was heated at 130° C. for 2×5 min in a microwave oven. The resulting mixture was then cooled to room temperature and diluted with tetrahydrofuran, stirred and filtered. The filter cake was washed with tetrahydrofuran and the combined filtrate and washings were concentrated in vacuo. Flash chromatography (ethyl acetate/heptane) afforded 361 mg (81%) N-(7-methoxy-4-phenyl-thiazolo[5,4-c]pyridin-2-yl)-benzamide as a white solid. ES-MS m/e (%): 362 (M+H+, 100).

Workup

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. filtrationfiltered
  3. washThe filter cake was washed with tetrahydrofuran
  4. concentrationthe combined filtrate and washings were concentrated in vacuo

Sources & evidence

ORD record
ord-8b364eabef674f889eeab665edaefd55
Source dataset
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07273865B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes