Potassium Carbonate → 4'-(tert-Butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-ylamine

HRID 1375221Notes

Reaction equation

HRID 1375221 reaction equation
[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10](B(O)O)=[CH:9][C:8]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].I[C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[NH2:33].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]([Si:5]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:31]2[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=2[NH2:33])=[CH:9][C:8]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 119952-IodoanilineHCID 21079851(4-{[tert-Butyl(diphenyl)silyl]oxy}-3-methoxyphenyl)boronic acid

Product 1

HCID 112480034'-(tert-Butyl-diphenyl-silanyloxy)-3'-methoxy-biphenyl-2-ylamine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17.89 g (44.0 mmol) 4-(tert-butyl-diphenyl-silanyloxy)-3-methoxy-phenyl-boronic acid, 6.89 g (31.45 mmol) 2-iodoaniline, 17.4 g (125.8 mmol) K2CO3 and 425 mg (6 mol %) Pd(OAc)2 in 140 ml THF and 80 ml H2O is heated to reflux for 20 hours. After cooling the mixture is filtrated over cellite and concentrated. The residue is dissolved in ethyl acetate and washed with water. After drying (MgSO4) and evaporating the solvent, the residue is subjected to flash-chromatography (ethyl acetate/hexane 1:9). Yield: 4′-(tert-Butyl-diphenyl-silanyloxy)-3′-methoxy-biphenyl-2-ylamine is isolated as a colorless oil.

Workup

  1. temperatureto reflux for 20 hours
  2. temperatureAfter cooling the mixture
  3. filtrationis filtrated over cellite
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with water
  7. dry with materialAfter drying (MgSO4)
  8. customevaporating the solvent

Sources & evidence

ORD record
ord-b7e334763dda439dbd8c8514646d03d7
Source dataset
uspto-grants-2007_01
Patent number
US07166746B2

Reaction notes

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