Potassium Carbonate → HCID 90417056, compound

HRID 588273Notes

Reaction equation

HRID 588273 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.CC1(C)C(C)(C)OB([C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C([O-])(O)=O.[Na+].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>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=3)[CH:3]=2)[NH:7]1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 6111935-Bromo-2-oxindoleHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 90417056HCID 90417056, compoundYield 102.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 5-bromoindolin-2-one (600 mg, 2.83 mmol) in 1,4-Dioxane (9 ml) and H2O (3 ml) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.05 g, 3.40 mmol), Pd(PPh3)4 (164 mg, 0.142 mmol) and K2CO3 (1.17 g, 8.50 mmol). After stirring at 120° C. in microwave reactor for 1 h, the reaction mixture was diluted with sat. NaHCO3 aq. and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give tert-butyl 4-(2-oxoindolin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (912 mg) as mixture with triphenylphosphin oxide.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-d5fc950e0e454d528c9bca429e1fc867
Source dataset
uspto-grants-2016_01
Patent number
US09227962B2

Reaction notes

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