Potassium Acetate → methyl 6-chloro-5-[4-(2-oxopyrrolidin-1-yl)phenyl]-1H-indole-3-carboxylate

HRID 1054716Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1.[CH3:14][O:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][C:23]([Cl:35])=[C:24](B3OCC(C)(C)CO3)[CH:25]=2)[NH:20][CH:19]=1)=[O:17].C([O-])(=O)C.[K+]>O1CCOCC1>[Cl:35][C:23]1[CH:22]=[C:21]2[C:26]([C:18]([C:16]([O:15][CH3:14])=[O:17])=[CH:19][NH:20]2)=[CH:25][C:24]=1[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 1-(4-bromophenyl)pyrrolidin-2-one (120 mg, 0.50 mmol), methyl-6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (160 mg, 0.50 mmol) and potassium acetate (147 mg, 1.50 mmol) in 1,4-dioxane (3 mL) was added PddppfCl2 (36.5 mg, 0.050 mmol). The mixture was degassed and purged with nitrogen for 5 minutes, then allowed to heat to 100° C. and stirred under microwave irradiation for 40 minutes. The reaction mixture was concentrated in vacuo to give a brown residue. The residue was purified by combi flash silica gel chromatography to give the title compound (112 mg, 61% yield) as a white solid.

Workup

additionwas added
customThe mixture was degassed
custompurged with nitrogen for 5 minutes
concentrationThe reaction mixture was concentrated in vacuo
customto give a brown residue
customThe residue was purified by combi flash silica gel chromatography

Sources & evidence

ORD record: ord-1a7fa0b5869e4fcb953a2696955b4547
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394285B2

Reaction notes

Loading…