Water → 3-[(4-Fluoro-2-methylphenyl)(4-fluorophenyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561584Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)O)=[C:4]([CH3:17])[CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].ClC1C=C(Cl)C=CC=1C([C:34]1[C:42]2[C:37](=[C:38]([CH2:44][S:45][CH3:46])[CH:39]=[C:40](F)[CH:41]=2)[NH:36][CH:35]=1)CCO.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:34]2[C:42]3[C:37](=[C:38]([CH2:44][S:45][CH3:46])[CH:39]=[CH:40][CH:41]=3)[NH:36][CH:35]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

509 mg (2.17 mmol) of the compound from Example 82A and 437 mg (1.97 mmol) of indium(III) chloride were added to 350 mg (1.97 mmol) of the compound from Example 8 in 15 ml of toluene. The reaction mixture was stirred at 80° C. for 5 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate, and the solid was filtered off. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 174 mg (22% of theory) of the title compound.

Workup

temperatureAfter cooling to RT
filtrationthe solid was filtered off
customThe phases of the filtrate were separated
extractionthe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record: ord-582347a2ca0841c687b16d7d189cb27a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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