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

HRID 338373Notes

Reaction equation

HRID 338373 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

5

Reactant 3

HCID 517044Potassium AcetateHCID 7361101-(4-Bromophenyl)pyrrolidin-2-oneHCID 86698665methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate

Product 1

HCID 86698716methyl 6-chloro-5-[4-(2-oxopyrrolidin-1-yl)phenyl]-1H-indole-3-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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 purgerd 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

  1. additionwas added
  2. customThe mixture was degassed
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto give a brown residue
  5. customThe residue was purified by combi flash silica gel chromatography

Sources & evidence

ORD record
ord-7a51ae225c804021aa8014ad6ecfdf6a
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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