Stannane → 3-(Furan-2-yl)-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

HRID 276763

반응식

HRID 276763 반응식
Br[C:2]1[C:3]([O:17][CH2:18][C:19]2[N:23]([CH3:24])[N:22]=[CH:21][N:20]=2)=[N:4][N:5]2[C:10]=1[CH:9]=[N:8][N:7]=[C:6]2[C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1.C([Sn](CCCC)(CCCC)[C:30]1[O:31][CH:32]=[CH:33][CH:34]=1)CCC.[SnH4]>O1CCOCC1.[Pd]>[O:31]1[CH:32]=[CH:33][CH:34]=[C:30]1[C:2]1[C:3]([O:17][CH2:18][C:19]2[N:23]([CH3:24])[N:22]=[CH:21][N:20]=2)=[N:4][N:5]2[C:10]=1[CH:9]=[N:8][N:7]=[C:6]2[C:11]1[CH:15]=[C:14]([CH3:16])[O:13][N:12]=1

참가 물질

6

반응물 3

HCID 123161StannaneHCID 43936882-(Tributylstannyl)furanHCID 226291463-Bromo-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2, 4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine

생성물 1

HCID 226291403-(Furan-2-yl)-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine수율 196.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 312751,4-Dioxane용매

실험 절차

A stirred mixture of 3-bromo-7-(5-methylisoxazol-3-yl)-2-(1-methyl-1H-[1,2,4]triazol-5-ylmethoxy)pyrazolo[1,5-d][1,2,4]triazine (Example 7) (80 mg, 0.20 mmol) in dioxan (10 mL) containing 2-tri-n-butylstannylfuran (146 mg, 0.41 mmol) was degassed with nitrogen for 20 min. Tetrakis-triphenylphosphine palladium(0) (50 mg) and copper(I)iodide (5 mg) were added and the mixture heated at reflux for 8 h. Further stannane (146 mg, 0.41 mmol) and palladium catalyst (50 mg) were added and the mixture heated at reflux for 16 h. The solvent was evaporated and the residue purified on silica eluting with 5% MeOH/DCM to give a yellow solid (149 mg). The yellow solid was re-chromatographed on silica eluting with 5% MeOH/DCM to give a yellow solid (29 mg) which was triturated with diethylether to give the title compound (15 mg, 19%) as a yellow solid. mp 226-228° C. 1H NMR (360 MHz, CDCl3) δ1.58 (9H, s), 2.61 (3H, s), 4.10 (3H, s), 5.78 (2H, s), 6.52-6.56 (1H, m), 6.75-6.79 (1H, m), 6.96 (1H, s), 7.57 (1H, s), 7.91 (1H, s), 9.71 (1H, s). Found: C, 52.68; h, 3.47; N, 28.64; C17H14N8O3.0.05(CH2Cl2).0.25(H2O) requires: C, 52.90; H, 28.95%.

후처리

  1. customwas degassed with nitrogen for 20 min
  2. additionTetrakis-triphenylphosphine palladium(0) (50 mg) and copper(I)iodide (5 mg) were added
  3. temperaturethe mixture heated
  4. temperatureat reflux for 8 h
  5. temperaturethe mixture heated
  6. temperatureat reflux for 16 h
  7. customThe solvent was evaporated
  8. customthe residue purified on silica eluting with 5% MeOH/DCM

출처 및 근거

ORD 기록
ord-a07aef879027416f8f6d1cfa8487eda3
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355638B1

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