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

HRID 2306598
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HRID 2306598 반응식
BrCCBr.[CH2:5](I)[C:6]([CH3:9])([CH3:8])[CH3:7].Br[C:12]1[C:17]([O:18][CH2:19][C:20]2[N:21]([CH3:25])[N:22]=[CH:23][N:24]=2)=[N:16][N:15]2[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])=[N:27][N:28]=[C:14]2[CH:13]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>CN(C=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH3:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:12]1[C:17]([O:18][CH2:19][C:20]2[N:21]([CH3:25])[N:22]=[CH:23][N:24]=2)=[N:16][N:15]2[C:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[F:35])=[N:27][N:28]=[C:14]2[CH:13]=1
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참가 물질

9

반응물 4

HCID 78391,2-DibromoethaneHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 521585Tris(furan-2-yl)phosphaneHCID 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 226098947-(2,2-dimethylpropyl)-3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,4-triazolo[4,3-b]pyridazine수율 58.1%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

1,2-Dibromoethane (0.03 ml, 10 mol %) was added to a stirred suspension of acid washed zinc dust (0.45 g, 7.0 mmol) in anhydrous DMF (3 ml) at 50° C. under nitrogen. After 5 min, neopentyl iodide (1.0 ml, 7.5 mmol) was added. The mixture was stirred for 2.5 h to give a grey-green milky solution. A mixture of 7-bromo-3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,4-triazolo[4,3-b]pyridazine (0.35 g, 0.866 mmol), tri-2-furylphosphine (0.08 g, 40 mol %) and tris(dibenzylideneacetone)dipalladium(0) (0.04 g, 5 mol %) in anhydrous DMF (2 ml) was stirred at 50° C. under nitrogen for 15 min followed by addition of the solution of organozinc reagent via syringe. After 2.5 h, the mixture was cooled, poured into water (100 ml) and extracted with dichloromethane (2×50 ml). The extracts were dried (Na2SO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 2% methanol-dichloromethane, gave a brown solid that was recrystallised from ethyl acetate-diethyl ether to give 7-(2,2-dimethylpropyl)-3-(2-fluorophenyl)-6-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,4-triazolo[4,3-b]pyridazine (0.199 g, 58%) as a beige powder; 1H NMR (360 MHz, CDCl3) δ 0.96 (9H, s), 2.61 (2H, s), 3.83 (3H, s), 5.47 (2H, s), 7.28 (1H, dd, J=10 and 10 Hz), 7.36 (1H, dd, J=8 and 8 Hz), 7.56-7.62 (1H, m), 7.83 (1H, s), 7.86 (1H, dd, J=8 and 8 Hz), 7.90 (1H, s); MS (ES+) m/e 396 [MH]+. Anal. Found C, 59.66; H, 5.69; N, 24.41%. C20H22FN7O.0.4H2O requires C, 59.66; H, 5.71; N, 24.35%.

후처리

  1. customto give a grey-green milky solution
  2. stirringwas stirred at 50° C. under nitrogen for 15 min
  3. waitAfter 2.5 h
  4. temperaturethe mixture was cooled
  5. extractionextracted with dichloromethane (2×50 ml)
  6. dry with materialThe extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washFlash column chromatography on silica gel, eluting with 2% methanol-dichloromethane
  10. customgave a brown solid that
  11. customwas recrystallised from ethyl acetate-diethyl ether

출처 및 근거

ORD 기록
ord-d3aeb0a9598e4f7fb3f2f7f2674e7ab6
출처 데이터셋
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06828322B2

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