Potassium Carbonate → 3-((2-Amino-4-chlorophenyl)thio)-1-(pyrrolidin-1-yl)propan-1-one

HRID 70450

Reaction equation

C([O-])([O-])=O.[K+].[K+].[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:13][CH2:14][C:15](Cl)=[O:16].[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[SH:26]>C1COCC1.O>[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[S:26][CH2:13][CH2:14][C:15]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:16]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of K2CO3 (3.6 g, 26 mmol) in THF (20 ml) was added pyrrolidine (2.1 ml, 26 mmol) at room temperature, then the mixture was cooled to −78° C. and 3-bromopropanoyl chloride (1.0 g, 5.83 mmol) was added slowly. After it was stirred for 30 min, 2-amino-4-chlorobenzenethiol (837 mg, 5.24 mmol) was added to the mixture and the reaction was stirred at room temperature for 3 hours. The mixture was diluted with water, extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0˜30% EtOAc in hexane) to yield the title compound (760 mg, 46%).

Workup

stirringthe reaction was stirred at room temperature for 3 hours
extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography on silica gel (0˜30% EtOAc in hexane)

Sources & evidence

ORD record: ord-407ee69d0d2446c7b08cd2559c4e95aa
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822530B2

Linked notes

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