Bromide ion → [4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]cyanamide

HRID 1993956Notes

Reaction equation

HRID 1993956 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[CH:4][CH:3]=1.[CH3:11][N:12]1[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[C:13]1B(O)O.[F-].[K+].[Br-]>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].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C1COCC1>[C:17]([C:16]1[N:12]([CH3:11])[C:13]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[CH:4][CH:3]=2)=[CH:14][CH:15]=1)#[N:18]

Participants

8

Reactant 4

HCID 259Bromide ionHCID 522689Potassium FluorideHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 122959414-bromophenylcyanamide

Product 1

HCID 71423729[4-(5-Cyano-1-methyl-1H-pyrrol-2-yl)phenyl]cyanamideYield 33.7%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-bromophenylcyanamide (0.651 g, 3.34 mmol), tris(dibenzylideneacetone)dipalladium (76 mg, 0.078 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. tri-Tert-butylphosphine (10 wt % in hexane) (0.486 mL, 0.078 mmol) was added to the mixture and allowed to stir 3 hours at 50° C. until the starting bromide was consumed. The mixture was then diluted with 1/1 hexane/ethylacetate, filtered through a plug of silica gel, the solvent was evaporated and the residue was flash chromatographed using 5/1, 4/1, then 3/2 Hexane/Ethylacetate to give (0.250 g, 33%) of the title compound.

Workup

  1. customvial fitted with a septa
  2. additionwas added
  3. customwas consumed
  4. additionThe mixture was then diluted with 1/1 hexane/ethylacetate
  5. filtrationfiltered through a plug of silica gel
  6. customthe solvent was evaporated
  7. customchromatographed

Sources & evidence

ORD record
ord-333340a3a6e04be082fe123ef6e05d3d
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

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