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

HRID 62802

Reaction equation

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

Participants

Conditions

Temperature: 135 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-483986f06f95406a93e695fb7c939545
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447041B2

Linked notes

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