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

HRID 917462
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인쇄 미리보기

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HRID 917462 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 1140Toluene용매
HCID 8028Tetrahydrofuran용매

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온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8b364eabef674f889eeab665edaefd55
출처 데이터셋
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07273865B2

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