Ethyl Acetate → methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate

HRID 2068878ノート

反応式

HRID 2068878 の反応式
[CH3:1][C:2]1([CH3:24])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:11]3[NH:12][C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=4)[C:5]=2[CH2:4][CH2:3]1.[H-].[Na+].[CH3:27][Si:28]([CH3:35])([CH3:34])[CH2:29][CH2:30][O:31][CH2:32]Cl.[C:36]([O:39][CH2:40]C)(=O)[CH3:37]>CN(C)C=O.O>[CH3:1][C:2]1([CH3:24])[CH2:10][C:9]2[N:8]([CH2:32][O:31][CH2:30][CH2:29][Si:28]([CH3:35])([CH3:34])[CH3:27])[N:7]=[C:6]([C:11]3[N:12]([CH2:40][O:39][CH2:36][CH2:37][Si:28]([CH3:34])([CH3:29])[CH3:27])[C:13]4[C:18]([CH:19]=3)=[CH:17][CH:16]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=4)[C:5]=2[CH2:4][CH2:3]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 136127476methyl 2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-6-carboxylate

生成物 1

HCID 58550118methyl 2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indole-6-carboxylate収率 80%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Under an argon atmosphere, to a solution of methyl 2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)indole-6-carboxylate (23 g, 71 mmol) in N,N-dimethylformamide (230 ml) was added sodium hydride (6.3 g, 157 mmol) in portions of about 500 mg at an inside temperature of −10° C., and the mixture was stirred for 30 min. Then, 2-(trimethylsilyl)ethoxymethyl chloride (26 g, 157 mmol) was added dropwise over 15 min, and the mixture was further stirred for 2 hr. To the reaction mixture were added ethyl acetate and water, and the organic layer was separated. Then, the organic layer was washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (33 g, yield 80%).

後処理

  1. stirringthe mixture was further stirred for 2 hr
  2. customthe organic layer was separated
  3. washThen, the organic layer was washed successively with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-fdd37e1d38ac4206bc6909a6d35ff89d
出典データセット
uspto-grants-2012_10
特許番号
US08299070B2

反応ノート

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