indium(III)chloride → Ethyl 3-(4-chlorophenyl)-3-cyclopropyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propanoate

HRID 561441Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:16]2[CH2:18][CH2:17]2)(O)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].[CH3:23][S:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:16]2[CH2:18][CH2:17]2)([C:31]2[C:30]3[C:34](=[C:26]([CH2:25][S:24][CH3:23])[CH:27]=[CH:28][CH:29]=3)[NH:33][CH:32]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

700 mg (2.61 mmol) of the compound from Example 90A and 576 mg (2.61 mmol) of indium(III) chloride were added to 462 mg (2.61 mmol) of the compound from Example 8A in 11 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the solid was filtered off through silica gel, and the solvents were removed in a rotary evaporator. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 69 mg (6% of theory) of the title compound.

Workup

temperatureAfter cooling to RT
filtrationthe solid was filtered off through silica gel
customthe solvents were removed in a rotary evaporator
customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-99ebdc481bce4b118fde08b658bff234
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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