Sodium Hydroxide → 5-Bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

HRID 338457ノート

反応式

HRID 338457 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][N:6]=[CH:5]2.C1(C(N)C2CCCCC2)CCCCC1.[CH3:26][Si:27]([CH2:30][CH2:31][O:32][CH2:33]Cl)([CH3:29])[CH3:28].[OH-].[Na+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:33][O:32][CH2:31][CH2:30][Si:27]([CH3:29])([CH3:28])[CH3:26])[N:7]=2)[CH:3]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10774245alpha-CyclohexylcyclohexanemethanamineHCID 247292595-Bromo-6-methyl-1H-indazole

生成物 1

HCID 866987925-Bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole収率 79%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-bromo-6-methyl-indazole (500 mg, 2.37 mmol) in THF (6 mL) was added dicyclohexylmethylamine (0.63 mL, 3.0 mmol), followed by SEM-chloride (0.50 mL, 2.8 mmol) via syringe. The reaction mixture was stirred at room temperature for 3 hours. EtOAc (20 mL) was added followed by 0.5N aqueous NaOH (15 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were washed consecutively with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (0-33% EtOAc/heptane) to provide the title compound (639 mg, 79% yield). MS (ES+) 343.1 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.03 (s, 1H), 7.93 (s, 1H), 7.60 (s, 1H), 5.70 (s, 2H), 3.62 (t, J=8.10 Hz, 2H), 2.52 (s, 3H), 0.95 (t, J=8.30 Hz, 2H), 0.00 (s, 9H).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed consecutively with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (0-33% EtOAc/heptane)

出典と根拠

ORDレコード
ord-6504a466430b4beead312fd2420a6814
出典データセット
uspto-grants-2014_11
特許番号
US08889730B2

反応ノート

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