2,6-Lutidine → 1-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde

HRID 456140ノート

反応式

HRID 456140 の反応式
[CH:1]([C:3]1[N:8]=[C:7]2[N:9]([CH2:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[N:19]=[CH:18][CH:17]=[CH:16]4)[N:10]=[N:11][C:6]2=[N:5][CH:4]=1)=C.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:32].[Na+]>O.O1CCOCC1.[Os](=O)(=O)(=O)=O>[N:19]1[C:20]2[C:15](=[CH:14][C:13]([CH2:12][N:9]3[C:7]4=[N:8][C:3]([CH:1]=[O:32])=[CH:4][N:5]=[C:6]4[N:11]=[N:10]3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 593418146-((6-Vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

生成物 1

HCID 866520351-(Quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine-6-carbaldehyde収率 2,233.8%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 6-((6-vinyl-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (100 mg, 0.347 mmol) and 2,6-dimethylpyridine (74.3 mg, 0.694 mmol), was added a solution of osmium(VIII) oxide (297 mg, 1.387 mmol) in H2O (1.333 mL), followed by a solution of sodium periodate (88 mg, 6.94 μmol) in 1,4-Dioxane (4 ml). The reaction mixture was stirred at rt for 10 h. The solvents was removed in vacuo and DCM was added to dilute the residue. The resulting solution was washed with saturated NaHCO3, NH4Cl and brine. The organic layer was separated, dried over Na2SO4, and concentrated to give a crude product, which was purified with Analogix gel silica (Hexanes:EA) to afford 45 mg of title compound in 43% yield. LCMS (method B): [MH]+=291, tR=1.00 min.

後処理

  1. customThe solvents was removed in vacuo and DCM
  2. additionwas added
  3. additionto dilute the residue
  4. washThe resulting solution was washed with saturated NaHCO3, NH4Cl and brine
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give a crude product, which
  9. customwas purified with Analogix gel silica (Hexanes:EA)

出典と根拠

ORDレコード
ord-788220e632784a09bf31297138bb8ce1
出典データセット
uspto-grants-2013_07
特許番号
US08497368B2

反応ノート

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