indium(III)chloride → 3-[1-(4-Chlorophenyl)-1-(2,2-difluorocyclopropyl)ethyl]-7-[(methylsulfanyl)methyl]-2,3-dihydro-1H-indole

HRID 561630Notes

Reaction equation

[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[Cl-].[In+3].[Cl-].[Cl-].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH:27]2[CH2:29][C:28]2([F:31])[F:30])(O)[CH3:25])=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]([CH:9]2[C:8]3[C:12](=[C:4]([CH2:3][S:2][CH3:1])[CH:5]=[CH:6][CH:7]=3)[NH:11][CH2:10]2)([CH:27]2[CH2:29][C:28]2([F:30])[F:31])[CH3:25])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

76.2 mg (0.43 mmol) of the compound from Example 8A, dissolved in 1 ml of toluene, were added to 190 mg (0.86 mmol) of indium(III) chloride and 100 mg (0.43 mmol) of the compound from Example 134A in 1 ml of toluene at RT, and the mixture was stirred at 80° C. for 2 h. Then a further 1.90 g (8.60 mmol) of indium(III) chloride were added, and the mixture was stirred at 80° C. for 1 h. It was diluted with toluene and washed with water, and the organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 16.0 mg (10% of theory) of the title compound as mixture of diastereomers.

Workup

stirringthe mixture was stirred at 80° C. for 1 h
washwashed with water
dry with materialthe organic phase was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record: ord-acc6fa86c5f34bcfab76440eac052748
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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