Nitrogen → 4-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-butyric acid ethyl ester

HRID 2075736Notes

Reaction equation

C(C(CCCC)COC(=O)CC[S:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][C:16]3[N:17]2[CH:20]=[N:21][N:22]=3)=[CH:12][CH:11]=1)C.N#N.CC(C)([O-])C.[K+].Br[CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47]>CN(C=O)C.CCOC(C)=O.O>[CH2:49]([O:48][C:46](=[O:47])[CH2:45][CH2:44][CH2:43][S:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][C:16]3[N:17]2[CH:20]=[N:21][N:22]=3)=[CH:12][CH:11]=1)[CH3:50]

Participants

Conditions

Temperature: 0 °C

Procedure

11c (100 mg, 0.21 mmol) in DMF (1 mL) was degassed for 5 minutes with N2, and then cooled to 0° C. under N2. Potassium tert-butoxide (29 mg, 0.26 mmol) in DMF (1 mL) was degassed for 5 minutes with N2, and then added to the solution of 11c. The reaction was warmed to room temperature, and LCMS analysis showed no starting material remained after 10 minutes. Ethyl 4-bromobutyrate (0.04 mL, 0.24 mmol) was added, and the mixture was stirred for 20 minutes. The reaction was diluted with EtOAc and water, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the desired product, 11d.

Workup

temperatureThe reaction was warmed to room temperature
extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e1c51ab50c5f422cb4dd27f271c1ddb8
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919621B2

Reaction notes

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