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

HRID 561577Notes

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.[F:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([CH2:25][S:26][CH3:27])[CH:24]=1)[NH:21][CH:20]=[CH:19]2.FC(F)(F)C(O)=O.[Cl-].[NH4+]>ClCCl>[CH:1]1([C:4]2([C:19]3[C:18]4[C:22](=[C:23]([CH2:25][S:26][CH3:27])[CH:24]=[C:16]([F:15])[CH:17]=4)[NH:21][CH:20]=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

633 mg (2.47 mmol) of the compound from Example 76A with a purity of 75% and 530 mg (2.71 mmol) of the compound from Example 11A were introduced into 12 ml of dichloromethane at 0° C., 0.23 ml (2.96 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 570 mg (63% 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-d30bdbcd611c46f2bdb36e3e3b9ab9d1
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

Loading…