Ethyl Acetate → 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)nicotinonitrile

HRID 506202ノート

反応式

HRID 506202 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[C:18]([C:19]#[N:20])=[CH:17][N:16]=[CH:15][C:14]=2I)[C:5]([CH3:11])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([Sn](CCCC)(CCCC)[C:27]1[O:28][C:29]2[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[CH:32][C:30]=2[CH:31]=1)CCC.C(OCC)(=O)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]2[C:18]([C:19]#[N:20])=[CH:17][N:16]=[CH:15][C:14]=2[C:27]2[O:28][C:29]3[CH:35]=[CH:34][C:33]([CH:36]=[O:37])=[CH:32][C:30]=3[CH:31]=2)[C:5]([CH3:11])=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 684470354-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-iodonicotinonitrileHCID 866168342-(Tributylstannyl)-1-benzofuran-5-carbaldehyde

生成物 1

HCID 866168374-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)nicotinonitrile収率 82.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a stirred solution of 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-iodonicotinonitrile (405 mg, 1 mmol) in DMF (7 mL) was added 2-(tributylstannyl)-1-benzofuran-5-carbaldehyde (609 mg, 1.4 mmol) and tetrakis(triphenylphosphine)palladium(0) (110 mg, 0.1 mmol) under nitrogen atmosphere, the reaction mixture was heated at 110° C. for 1.5 h and cooled to room temperature and ethyl acetate was added to the resulting mixture. The organic phase was washed with water, saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated and the residue was purified by flash column chromatography (ethyl acetate/hexane) to give 4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl)nicotinonitrile as a yellow solid (351 mg, 82%). HPLC retention time: 12.4 min.(g); and MS: 427.3 (M+H).

後処理

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe residue was purified by flash column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-899b3b2a063f428192d3cee8ff19b537
出典データセット
uspto-grants-2010_08
特許番号
US07781591B2

反応ノート

読み込み中…