Bromine → Ethyl 5-bromo-4-(3-cyano-4-fluorophenyl)-1,3-thiazole-2-carboxylate

HRID 2038376Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

At room temperature, 8.10 g (50.6 mmol) of bromine and 4.97 g (50.6 mmol) of potassium acetate are added to 1.40 g (5.07 mmol) of the compound from Example 28A in 80 ml of conc. acetic acid. The mixture is stirred at 100° C. for 48 h, whereby after 24 and 36 h, bromine (in each case 4.05 g, 25.3 mmol) and potassium acetate (in each case 2.49 g, 25.3 mmol) are again added. A 1M aqueous sodium thiosulfate solution is subsequently added, and the reaction solution is extracted with dichloromethane. The combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1). 1.55 g (84% of theory) of the title compound are obtained.

Workup

extractionthe reaction solution is extracted with dichloromethane
dry with materialThe combined organic phases are dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record: ord-852ec8dcc0cf43d3b493911a5e4724a9
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575357B2

Reaction notes

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