Trifluoroacetic acid → 3-(1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-yl)-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561576Notes

Reaction equation

[CH:1]1([C:4]2(O)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[CH3:15][S:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]2[C:26]=1[NH:25][CH:24]=[CH:23]2.FC(F)(F)C(O)=O.[Cl-].[NH4+]>ClCCl>[CH:1]1([C:4]2([C:23]3[C:22]4[C:26](=[C:18]([CH2:17][S:16][CH3:15])[CH:19]=[CH:20][CH:21]=4)[NH:25][CH:24]=3)[C:12]3[C:7](=[CH:8][C:9]([F:13])=[CH:10][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

200 mg (0.78 mmol) of the compound from Example 76A with a purity of 75% and 152 mg (0.86 mmol) of the compound from Example 8A were introduced into 3.8 ml of dichloromethane at 0° C., 0.07 ml (0.94 mmol) of trifluoroacetic acid was added, and the mixture was stirred at 0° C. for 4 h. It was diluted with dichloromethane and added to saturated aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were 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 175 mg (64% of theory) of the title compound.

Workup

customthe phases were separated
extractionthe aqueous phase was extracted with dichloromethane
dry with materialthe combined organic phases were 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-e386a73f1f9d40dcb05ae4cc9b4b5d17
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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