Potassium Carbonate → 3-(5-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrile

HRID 1777187Notes

Reaction equation

HRID 1777187 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[Si:13]([O:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25](Cl)[CH:24]=[CH:23][C:22]1=2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:13]([O:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25]([CH:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=4)[NH:3][C:2]3=[O:1])[CH:24]=[CH:23][C:22]1=2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86663635HCID 86663635, compound

Product 1

HCID 668235213-(5-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrileYield 40%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-oxoindoline-5-carbonitrile (30 mg, 0.190 mmol) in THF placed in a microwave vial were added sequentially 5-(tert-butyldimethylsilyloxy)-2-chloro-5,6,7,8-tetrahydroquinoline (67.8 mg, 0.228 mmol), K2CO3 (52.4 mg, 0.379 mmol), X-PHOS (7.23 mg, 0.015 mmol), and Pd2(dba)3 (3.47 mg, 3.79 μmol). The vial was sealed and flushed with argon. The mixture was heated in a microwave oven at 80° C. for 95 min. The mixture was cooled to RT and diluted with water and ethyl acetate. The organic layer was separated and the remaining aqueous layer was extracted with dichloromethane. The combined dichloromethane extracts were dried over sodium sulfate, filtered, and evaporated to dryness. Amount 32 mg. Yield 40%.

Workup

  1. customThe vial was sealed
  2. customflushed with argon
  3. temperatureThe mixture was cooled to RT
  4. additiondiluted with water and ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe remaining aqueous layer was extracted with dichloromethane
  7. dry with materialThe combined dichloromethane extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-19337b4fe9dd42de91dfe4152946e219
Source dataset
uspto-grants-2016_02
Patent number
US09266855B2

Reaction notes

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