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

HRID 917462
ノート
印刷プレビュー

反応式

HRID 917462 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 1140Toluene溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8b364eabef674f889eeab665edaefd55
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07273865B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート