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

反応式

HRID 276763 の反応式
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

参加物

6

反応物 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

生成物 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]triazine収率 196.9%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 312751,4-Dioxane溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-a07aef879027416f8f6d1cfa8487eda3
出典データセット
uspto-grants-2002_03
特許番号
US06355638B1

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