Dimethylformamide → 2-(3-Cyanophenyl)-4-(pyridin-2-yl)-1,3-thiazole

HRID 2216882노트

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HRID 2216882 반응식
I[C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:19][N:20](C)C=O>C1(C)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)#[N:20]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 101333442-(3-Iodophenyl)-4-(pyridin-2-yl)-1,3-thiazole

생성물 1

HCID 99651212-(3-Cyanophenyl)-4-(pyridin-2-yl)-1,3-thiazole수율 30%

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

A mixture of 2-(3-iodophenyl)-4-(pyridin-2-yl)-1,3-thiazole (1–30 mg, 0.36 mmol), zinc cyanide (117 mg, 1.0 mmol) and Pd(PPh3)4 (10 mg, 0.009 mmol) in N,N-dimethylformamide (2 mL) was heated overnight at 80° C. The mixture was cooled and diluted with toluene (5 mL). The organic solution was washed with 2N NH4OH (2×10 mL). The mixture was then extracted with ethyl acetate and the organic extract was washed with brine. The organic solution was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel chromatography afforded 28 mg (30%) of 2-(3-cyanophenyl)-4-(pyridin-2-yl)-1,3-thiazole: 1H-NMR (CDCl3), ppm: 8.65. (d, 1H), 8.38 (s, 1H), 8.25 (m, 2H), 8.15 (s, 1H), 7.85 (m, 1H), 7.72 (m, 1H), 7.6 (t, 1H), 7.28 (m, 1H). GC/EI-MS gave m/z 263 (M+).

후처리

  1. temperatureThe mixture was cooled
  2. washThe organic solution was washed with 2N NH4OH (2×10 mL)
  3. extractionThe mixture was then extracted with ethyl acetate
  4. extractionthe organic extract
  5. washwas washed with brine
  6. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-2c3c5e4c746b4b72988cd11efc9b6d03
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112595B2

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