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Trifluoroiodomethane → 3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-7-trifluoromethyl-1,2,4-triazolo[4,3-b]pyridazine

HRID 2306605
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HRID 2306605 반응식
I[C:2]([F:5])([F:4])[F:3].Br[C:7]1[C:12]([O:13][CH2:14][C:15]2[N:16]([CH3:20])[N:17]=[CH:18][N:19]=2)=[N:11][N:10]2[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:22][N:23]=[C:9]2[CH:8]=1>CN(C=O)C.ClCCl.[Cu]>[F:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[N:10]2[N:11]=[C:12]([O:13][CH2:14][C:15]3[N:16]([CH3:20])[N:17]=[CH:18][N:19]=3)[C:7]([C:2]([F:5])([F:4])[F:3])=[CH:8][C:9]2=[N:23][N:22]=1
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참가 물질

6

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HCID 16843TrifluoroiodomethaneHCID 154861777-bromo-3-(2-fluorophenyl)-6-(2-methyl2H-1,2,4-triazol-3-ylmethoxy)-1,2,4-triazolo[4,3-b]pyridazine

생성물 1

HCID 226099083-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-7-trifluoromethyl-1,2,4-triazolo[4,3-b]pyridazine수율 6.2%

시약·촉매·용매 3

HCID 23978Copper촉매HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

Iodotrifluoromethane (2.0 g, 10 mmol) was bubbled through a solution of 7-bromo-3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,4-triazolo[4,3-b]pyridazine (0.10 g, 0.25 mmol) in dry DMF (2 ml) at room temperature until the required quantity of gas had dissolved. Copper powder (0.16 g, 2.5 mmol) was added and the mixture was stirred in a sealed tube at 80° C. for 18 h. The mixture was cooled, diluted with dichloromethane (50 ml) and filtered. The filtrate was washed with water (50 ml), then dried (Na2SO4), filtered and concentrated. Preparative thin layer chromatography, eluting with 3% methanol-dichloromethane, gave 3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-7-trifluoromethyl-1,2,4-triazolo[4,3-b]pyridazine (0.0061 g, 6%) as a pale yellow solid; m.p. 123-126° C.; 1H NMR (360 MHz, CDCl3) δ 3.92 (3H, s), 5.60 (2H, s), 7.31 (1H, dd, J=8 and 8 Hz), 7.40 (1H, dd, J=8 and 8 Hz), 7.56-7.64 (1H, m), 7.86-7.94 (2H, m), 8.50 (1H, s); MS (ES+) m/e 393 [MH]+.

후처리

  1. dissolutionhad dissolved
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washThe filtrate was washed with water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washPreparative thin layer chromatography, eluting with 3% methanol-dichloromethane

출처 및 근거

ORD 기록
ord-f9e900de25bb48de8949d5c752c0f95a
출처 데이터셋
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06828322B2

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