Tetraethoxysilane → Ethyl 2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

HRID 707772

反応式

HRID 707772 の反応式
I[C:2]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:11]([O:13][C:14](=[O:22])[CH2:15][CH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O)[CH3:12].[Si](OCC)(OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:3]2[NH:4][C:17]3[CH:16]([CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:22])[CH2:20][CH2:19][C:18]=3[C:2]=2[CH:8]=1

参加物

8

反応物 5

HCID 6517TetraethoxysilaneHCID 81531DiisopropylethylamineHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 2723663Ethyl 2-(2-oxocyclopentyl)acetateHCID 110103362-Iodo-4-methoxyphenylamine

生成物 1

HCID 67211141Ethyl 2-(7-methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

試薬・触媒・溶媒 2

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

反応条件

温度
135 °C

実験手順

To a solution of 2-iodo-4-methoxyaniline (20.0 g, 80 mmol), ethyl-2-(2-oxocyclopentyl)acetate (20.5 g, 120 mmol, 1.5 eq) and tetraethyl orthosilicate (21.7 g, 104 mmol, 1.3 eq) in anhydrous DMF (100 mL), was added pyridine p-toluenesulfonate (0.807 g, 3.21 mmol, 0.04 eq). The dark brown solution was stirred at 135° C. for 5 h under N2, allowed to cool to 100° C. and then added DIPEA (31.1 g, 241 mmol, 3 eq) followed by Pd(OAc)2 (0.541 g, 2.41 mmol, 0.03 eq). The resulting mixture was stirred at 120° C. for 22 h under N2, concentrated under reduced pressure. The residue was taken up in DCM, filtered through a plug of silica and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound. LCMS m/z=274.4 [M+H]+.

後処理

  1. temperatureto cool to 100° C.
  2. stirringThe resulting mixture was stirred at 120° C. for 22 h under N2
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-994ce924f0b94148bcde36a5dc8a8d15
出典データセット
uspto-grants-2015_11
特許番号
US09175320B2

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