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Triethylamine → 1-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

HRID 79296
ノート
印刷プレビュー

反応式

HRID 79296 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[N:16]=2)[N:3]=1.[CH:23]([B-](F)(F)F)=[CH2:24].[K+].C(N(CC)CC)C>CC(O)C.C1COCC1>[CH3:22][O:21][C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:23]=[CH2:24])=[N:3]2)[CH:20]=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 672611043-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole

生成物 1

HCID 672600471-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole収率 94.3%

試薬・触媒・溶媒 1

HCID 22597222Tetrahydrofuran 2-propanol溶媒

実験手順

To 3-iodo-1-((6-methoxypyridin-2-yl)methyl)-4-nitro-1H-indazole (2.65 g, 6.46 mmol) in IPA/THF (40 mL/10 mL) was added potassium vinyltrifluoroborate (1.30 g, 9.69 mmol), triethylamine (1.31 g, 12.9 mmol) and 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.264 g, 0.323 mmol). The reaction mixture was heated to reflux and stirred for 16 hours. The reaction mixture was cooled to ambient temperature and concentrated to remove solvent. The residue was dissolved with EtOAc (100 mL) and washed with saturated NH4Cl, H2O and brine. The solution was dried (Na2SO4) and concentrated to provide the desired product (1.89 g).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto remove solvent
  5. dissolutionThe residue was dissolved with EtOAc (100 mL)
  6. washwashed with saturated NH4Cl, H2O and brine
  7. dry with materialThe solution was dried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-50f8bd1d9677421285b40aec032841ed
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841455B2

反応ノート

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