Tris(1,1-dimethylethyl)phosphine → [4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)-2-methylphenyl]cyanamide

HRID 1993958Notes

Reaction equation

HRID 1993958 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][N:13]1[C:17]([C:18]#[N:19])=[CH:16][CH:15]=[C:14]1B(O)O.[F-].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>CCCCCC.C(OC(=O)C)C.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].C1COCC1>[C:18]([C:17]1[N:13]([CH3:12])[C:14]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=2)=[CH:15][CH:16]=1)#[N:19]

Participants

8

Reactant 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 62482653(4-Bromo-2-methylphenyl)cyanamide

Product 1

HCID 16037553[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)-2-methylphenyl]cyanamideYield 7.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

(4-bromo-2-methylphenyl)cyanamide (0.698 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium (76 mg, 0.083 mmol), N-methyl-5-cyanopyrroleboronic acid (1.1 g, 7.3 mmol), and potassium fluoride (0.776 g, 13.2 mmol) were placed in a 40 mL vial fitted with a septa. The vial was then filled with a continuous flow of nitrogen and THF (10 mL) was added with stirring. Then tri-tert-butylphosphine (10 wt % in hexane) (0.486 mL, 0.083 mmol) was added to the mixture and allowed to stir 3 hours. The mixture was then diluted with 1/1 hexane/ethylacetate and filtered through a plug of silica gel, the reaction was concentrated and the residue was flash chromatographed using 4/1 Hexane/THF to give (0.062 g, 7%) of the title compound.

Workup

  1. customvial fitted with a septa
  2. additionwas added
  3. stirringto stir 3 hours
  4. filtrationfiltered through a plug of silica gel
  5. concentrationthe reaction was concentrated
  6. customchromatographed

Sources & evidence

ORD record
ord-9e52db49cf384568a06b6c983110fd93
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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