Dichloromethane → 1-(Phenylacetyl)-5-(4-pyridinyl)indoline

HRID 1510253Notes

Reaction equation

HRID 1510253 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][CH2:5]2.CC1(C)C(C)(C)OB([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)O1.ClCCl.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:13]1([CH2:12][C:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)=[O:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 668241055-bromo-1-(phenylacetyl)-2,3-dihydro-1H-indole

Product 1

HCID 576639941-(Phenylacetyl)-5-(4-pyridinyl)indolineYield 50.5%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-1-(phenylacetyl)indoline (15.98 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (12.4 g) in 1,2-dimethoxyethane (500 mL) were added [1,1′-bis-(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1.24 g) and potassium phosphate (32.2 g) at ambient temperature and the mixture was stirred at 100° C. for 60 hours. The mixture was evaporated in vacuo to remove 1,2-dimethoxyethane and the residue was dissolved in a mixture of ethyl acetate (600 mL) and water (300 mL). The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 1-(phenylacetyl)-5-(4-pyridinyl)indoline (8.02 g) as a white powder.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customto remove 1,2-dimethoxyethane
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate (600 mL) and water (300 mL)
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-ddba1c18feda415aba0fbfac60cffdf3
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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