Potassium Cyanide → HCID 58392535, compound

HRID 561547Notes

Reaction equation

Cl[CH2:2][CH2:3][CH:4]([C:12]1[C:20]2[C:15](=[C:16]([CH2:22][S:23][CH3:24])[CH:17]=[C:18]([F:21])[CH:19]=2)[NH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[C-:25]#[N:26].[K+]>CS(C)=O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH:4]([C:12]2[C:20]3[C:15](=[C:16]([CH2:22][S:23][CH3:24])[CH:17]=[C:18]([F:21])[CH:19]=3)[NH:14][CH:13]=2)[CH2:3][CH2:2][C:25]#[N:26])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

180 mg (0.47 mmol) of 3-[3-chloro-1-(4-chlorophenyl)propyl]-5-fluoro-7-[(methylsulfanyl)methyl]-1H-indole and 61.3 mg (0.94 mmol) of potassium cyanide were dissolved in 11 ml of DMSO and stirred at 120° C. overnight. The mixture was concentrated, and the residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in a further 140 mg (80% of theory) of the title compound and thus in an overall yield of the title compound of 242 mg (64% of theory).

Workup

concentrationThe mixture was concentrated
washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

Sources & evidence

ORD record: ord-228b892d20ee44b6a501c3087f81e383
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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