Potassium Carbonate → 1-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrile

HRID 907159ノート

反応式

HRID 907159 の反応式
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][CH2:31][CH2:32]Br>CN(C=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:32][CH2:31][O:30][CH3:29])=[CH:20][CH:21]=1)[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 594253351-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

生成物 1

HCID 594260301-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrile収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-Ethyl-2-(4-hydroxy-phenyl)-6-methoxy-1H-indole-3-carbonitrile (40 mg, 0.14 mmol), prepared as in example 1Ga step B, was combined with K2CO3 (77 mg, 0.56 mmol), bromoethyl methyl ether (26 μL, 0.28 mmol), and DMF (450 μL). This was stirred at room temperature for 1 hour, and then at 75° C. for 3 hours. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (CH2Cl2, 0-5% EtOAc) to yield 1-ethyl-6-methoxy-2-[4-(2-methoxyethoxy)-phenyl]-1H-indole-3-carbonitrile (44 mg, 90%) as a white solid.

後処理

  1. waitat 75° C. for 3 hours
  2. customThe reaction mixture was then partitioned between H2O and EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (CH2Cl2, 0-5% EtOAc)

出典と根拠

ORDレコード
ord-220f9ee6196941ebb3c43b062ae6e062
出典データセット
uspto-grants-2011_09
特許番号
US08013006B2

反応ノート

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