Potassium Carbonate → 5-(1-Phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-one

HRID 588278Notes

Reaction equation

HRID 588278 reaction equation
FC(F)(F)S(O[C:7]1[CH2:8][CH2:9][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH:12]=1)(=O)=O.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[C:31]3[C:35](=[CH:36][CH:37]=2)[NH:34][C:33](=[O:38])[CH2:32]3)O1.[Li+].[Cl-].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]1([N:10]2[CH2:11][CH:12]=[C:7]([C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[NH:34][C:33](=[O:38])[CH2:32]4)[CH2:8][CH2:9]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 219314865-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-oneHCID 904187181-Phenyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate

Product 1

HCID 904177265-(1-Phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-oneYield 77%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-phenyl-1,2,3,6-tetrahydropyridin-4-yl trifluoromethanesulfonate (104 mg, 0.339 mmol) in 1,4-Dioxane (3 ml) and H2O (1 ml) were added 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (97.6 mg, 0.377 mmol), Pd(PPh3)4 (38.8 mg, 0.00336 mmol), LiCl (47.1 mg, 1.11 mmol) and K2CO3 (140 mg, 1.01 mmol). After stirring at 120° C. in microwave reactor for 1 h, the reaction mixture was quenched by sat. NaHCO3 aq. The resulting mixture was extracted with CHCl3, the organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give 5-(1-phenyl-1,2,3,6-tetrahydropyridin-4-yl)indolin-2-one (75.8 mg) as mixture of triphenylphosphine oxide.

Workup

  1. customthe reaction mixture was quenched by sat. NaHCO3 aq. The resulting mixture
  2. extractionwas extracted with CHCl3
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-61a53c8d3991471e9ffbcb1f04ffe745
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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