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

HRID 907159노트

반응식

HRID 907159 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-220f9ee6196941ebb3c43b062ae6e062
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013006B2

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