Aniline → Phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine

HRID 1716631Notes

Reaction equation

HRID 1716631 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C>[C:2]1([NH:1][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:22]([CH3:24])[CH3:23])([CH:25]([CH3:27])[CH3:26])[CH:19]([CH3:20])[CH3:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 27955734-bromo-1-(triisopropylsilyl)-1H-indole

Product 1

HCID 59831613Phenyl-(1-triisopropylsilanyl-1H-indol-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
110 °C

Procedure

Aniline (328 μl, 3.6 mmol) was added to a room temperature mixture of 4-bromo-1-triisopropylsilanyl-1H-indole (1.06 g, 3 mmol), tris(dibenzylideneacetone)dipalladium 2-(dicyclohexylphosphino)-2,4,6-triisopropyl-1,1′-biphenylphosphine (Pd2(dba)3, 27.5 mg, 0.03 mmol), (72 mg, 0.05 mmol) and K2CO3 (1.04 g, 7.5 mmol) in t-BuOH (14 ml). The reaction mixture was stirred at 110° C. for 4 hours. The reaction was cooled, and the solid was filtered off. The filtrate was concentrated and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording the compound XXI as a yellow oil in quantitative yield (1.09 g).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe solid was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was partitioned between EtOAc
  5. extractionThe aqueous layer was extracted twice with EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-0203741c513f402fbe2e422c0d910474
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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