Water → 4-(2-Bromo-1,3-thiazol-5-yl)-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrile

HRID 561557Notes

Reaction equation

[C-:1]#[N:2].[K+].CS(O[CH2:9][CH2:10][CH:11]([C:24]1[S:28][C:27]([Br:29])=[N:26][CH:25]=1)[C:12]1[C:20]2[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)(=O)=O.O>CN(C=O)C>[Br:29][C:27]1[S:28][C:24]([CH:11]([C:12]2[C:20]3[C:15](=[C:16]([CH2:21][S:22][CH3:23])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH2:10][CH2:9][C:1]#[N:2])=[CH:25][N:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

14 mg (0.21 mmol) of potassium cyanide were added to 50 mg (0.11 mmol) of the compound from Example 69A in 1 ml of DMF. The mixture was stirred at 80° C. for 5 h, water was added to the reaction solution, and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried over sodium sulfate, the solid was filtered off, and the solvents were removed. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 38 mg (89% of theory) of the target compound were obtained.

Workup

extractionthe aqueous phase was extracted twice with dichloromethane
dry with materialThe combined organic phases were dried over sodium sulfate
filtrationthe solid was filtered off
customthe solvents were removed
customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)
custom38 mg (89% of theory) of the target compound were obtained

Sources & evidence

ORD record: ord-3793f4490365454482c2a2940276fb1a
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

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