Ammonium Chloride → Methyl 1-cyclopentyl-3-methyl-2-trimethylsilylindole-5-carboxylate

HRID 1174638

反応式

HRID 1174638 の反応式
[CH:1]1([NH:6][C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=2I)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Li+].C([O-])(=O)C.[K+].[CH3:25][Si:26]([CH3:31])([CH3:30])[C:27]#[C:28][CH3:29].[Cl-].[NH4+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:1]1([N:6]2[C:7]3[C:8](=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=3)[C:28]([CH3:29])=[C:27]2[Si:26]([CH3:31])([CH3:30])[CH3:25])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 803631-(Trimethylsilyl)prop-1-yneHCID 433294Lithium ChlorideHCID 517044Potassium AcetateHCID 21974264Methyl 4-(N-cyclopentylamino)-3-iodobenzoate

生成物 1

HCID 21974273Methyl 1-cyclopentyl-3-methyl-2-trimethylsilylindole-5-carboxylate収率 75%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of methyl 4-(N-cyclopentylamino)-3-iodobenzoate from above (22.42 g, 65 mmol), palladium acetate (738 mg, 3.28 mmol), lithium chloride (2.757 g, 65 mmol), potassium acetate (12.757 g, 92.30 mmol), and 1-trimethylsilyl-1-propyne (28.70 mL, 192.56 mmol) in 390 mL of DMF was heated at 100° C. for 6 hours. The mixture was added onto 500 mL of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The ethyl acetate fraction was dried, evaporated and semi-purified by flash chromatography using silica gel and 0.1% ethyl acetate in hexane. Adding hexane to the semi-purified compound gave 16 g of white crystals (75%).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate fraction was dried
  3. customevaporated and semi-purified by flash chromatography

出典と根拠

ORDレコード
ord-ab026ffe0bed4ea493bfa38db6b99bed
出典データセット
uspto-grants-2010_11
特許番号
US07838537B2

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