Water → HCID 131733320, compound

HRID 515918Notes

Reaction equation

HRID 515918 reaction equation
Br[C:2]1[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[N:5]([CH3:7])[CH:6]=1.[Si:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.O>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[C:3]([CH3:10])=[C:4]([C:8]#[N:9])[N:5]([CH3:7])[CH:6]=2)=[CH:21][CH:20]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 117830788HCID 117830788, compound

Product 1

HCID 131733320HCID 131733320, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-1,3-dimethyl-1H-pyrrole-2-carbonitrile (2.03 g, 10.2 mmol) and 4-[(tert-butyldimethylsilyl)oxy]aniline (3.41 g, 15.3 mmol) are dissolved in toluene (40 mL). The solution is degassed with nitrogen for 10 minutes. Sodium tert-butylate (1.18 g, 12.2 mmol), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (0.17 g, 0.41 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.187 g, 0.2 mmol) are then added. The mixture is heated at 100° C. for 30 minutes and then cooled to ambient temperature. Water (50 mL) and Celite (6 g) are added. The suspension is filtered over Celite, and the filtrate is diluted with MTBE. The phases are separated and the aqueous phase is extracted with MTBE (2×50 mL). The combined organic phases are dried over Na2SO4 and filtered. The residue is purified by chromatography over silica gel using ethyl acetate and heptane as eluants followed by reverse-phase chromatography using methanol and water as eluants. The product obtained is lyophilised to provide the expected compound in the form of a solid.

Workup

  1. customThe solution is degassed with nitrogen for 10 minutes
  2. temperaturecooled to ambient temperature
  3. filtrationThe suspension is filtered over Celite
  4. additionthe filtrate is diluted with MTBE
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with MTBE (2×50 mL)
  7. dry with materialThe combined organic phases are dried over Na2SO4
  8. filtrationfiltered
  9. customThe residue is purified by chromatography over silica gel
  10. customThe product obtained

Sources & evidence

ORD record
ord-cc0ff917372948468611936b69a6b714
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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