Ammonium Chloride → (Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanol

HRID 69243

反応式

HRID 69243 の反応式
Br[C:2]1[N:6]2[N:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Mg]Br)C.[CH3:16][Si:17]([CH3:34])([CH3:33])[CH2:18][CH2:19][O:20][CH2:21][N:22]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27]([CH:31]=[O:32])=[CH:28]2)=[N:23]1.[NH4+].[Cl-]>C1COCC1.CCOCC>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([CH:31]([C:27]3[CH:26]=[CH:25][C:24]4[C:29](=[CH:30][N:22]([CH2:21][O:20][CH2:19][CH2:18][Si:17]([CH3:34])([CH3:33])[CH3:16])[N:23]=4)[CH:28]=3)[OH:32])=[CH:3][N:4]=2)[N:7]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazineHCID 866351152-(2-Trimethylsilanyl-ethoxymethyl)-2H-indazole-5-carbaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 87523362(Rac)-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-methanol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (465 mg, 2.0 mmol) in THF (60 mL) was added dropwise at rt a solution of ethylmagnesium bromide in Et2O (3 M, 1.0 mL). The temperature rose slightly (up to 27° C.) and the RM was stirred 15 min. Then a solution of 2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazole-5-carbaldehyde (Stage 150.4, 829 mg, 3.00 mmol) in THF (8 mL) was added dropwise and the RM was then stirred 2 h at rt. The RM was then taken into a solution of NH4Cl and extracted with EtOAc. Combined organic layers were washed with brine, dried over Na2SO4 and the solvent was removed. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=95:5->0:100) to afford the title compound as a light brown thick oil (tR 5.35 min (conditions 3), MH+=430).

後処理

  1. customup to 27° C.
  2. stirringthe RM was then stirred 2 h at rt
  3. extractionextracted with EtOAc
  4. washCombined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed
  7. customThe residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, n-hexane/EtOAc=95:5->0:100)

出典と根拠

ORDレコード
ord-8bf8342225db4c129d67bcdb92bccc82
出典データセット
uspto-grants-2014_09
特許番号
US08822468B2

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