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Cesium carbonate → 3-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrile

HRID 911059
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반응식

HRID 911059 반응식
[Br:1][C:2]1[C:3]([SH:22])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:13]=2)=[N:6][CH:7]=1.Cl[C:24]1[CH:31]=[N:30][CH:29]=[C:28]([Cl:32])[C:25]=1[C:26]#[N:27].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[C:3]([S:22][C:24]2[CH:31]=[N:30][CH:29]=[C:28]([Cl:32])[C:25]=2[C:26]#[N:27])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:13]=2)=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 111375993,5-Dichloropyridine-4-carbonitrileHCID 1785277275-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol

생성물 1

HCID 866347743-(5-Bromo-2-(4-phenethylthiazol-2-ylamino)pyridin-4-ylthio)-5-chloroisonicotinonitrile수율 49.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A flask was charged with 5-bromo-2-(4-phenethylthiazol-2-ylamino)pyridine-4-thiol (0.040 g, 0.10 mmol), 3,5-dichloroisonicotinonitrile (0.019 g, 0.11 mmol), Cs2CO3 (0.037 g, 0.11 mmol), and DMSO (2 mL). The reaction mixture was stirred at ambient temperature overnight, then quenched with water, extracted with EtOAc, dried, and concentrated. The crude material was purified by flash chromatography to provide the desired product (0.026 g, 48% yield) as a yellow solid. 1H NMR (CDCl3) δ 8.74 (d, 2H), 8.39 (s, 1H), 7.16-7.30 (m, 5H), 6.68 (s, 1H), 6.33 (s, 1H), 2.85-2.92 (m, 4H).

후처리

  1. customquenched with water
  2. extractionextracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-643023c9a1584667b838e04424a27ecd
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08022222B2

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