Bromobenzene → HCID 58230581, compound

HRID 390383Notes

Reaction equation

HRID 390383 reaction equation
[N:1]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][CH2:7]2)[CH2:3][CH2:2]1.Br[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[C:26]1([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]3([CH2:3][CH2:2][N:1]([C:15]([O:17][CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:16])[CH2:6][CH2:5]3)[CH2:7]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 7961BromobenzeneHCID 10796Cesium carbonateHCID 10914256Benzyl 1,2-dihydrospiro[indole-3,4'-piperidine]-1'-carboxylate

Product 1

HCID 58230581HCID 58230581, compoundYield 86.48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of benzyl spiro[indoline-3,4′-piperidine]-1′-carboxylate (1.5 g, 4.65 mmol) in 1-4, dioxane (5 mL) is added bromobenzene (0.803 g, 5.115 mmol), 4,5-(diphenyl-phosphino)-9,9-dimethyl xanthene (0.807 g, 1.395 mmol) and cesium carbonate (4.54 g, 13.95 mmol) at 0° C. The reaction mixture is purged with nitrogen gas for 15 minutes and palladium acetate (0.062 g, 0.279 mmol) is added. The mixture is stirred at 100° C. for 5 hours, filtered, diluted with ammonium chloride solution, extracted with EtOAc, dried with sodium sulphate, and concentrated under reduced pressure. The crude material is purified by silica gel chromatography, eluting with hexane:ethyl acetate (9.0:1.0) to give the title compound (1.6 g, 86.48%). ESI/MS m/z 399.4 (M+H)+.

Workup

  1. customThe reaction mixture is purged with nitrogen gas for 15 minutes
  2. filtrationfiltered
  3. additiondiluted with ammonium chloride solution
  4. extractionextracted with EtOAc
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material is purified by silica gel chromatography
  8. washeluting with hexane:ethyl acetate (9.0:1.0)

Sources & evidence

ORD record
ord-1e4b0a88d9954ecd800bb2c73cbd2a61
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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