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

HRID 1593574Notes

Reaction equation

HRID 1593574 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[C:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.[CH3:14][N:15]1[C:19]([C:20]#[N:21])=[CH:18][CH:17]=[C:16]1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[Br-]>C1COCC1>[C:20]([C:19]1[N:15]([CH3:14])[C:16]([C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9]#[N:10])=[C:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=2)=[CH:17][CH:18]=1)#[N:21]

Participants

7

Reactant 5

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acidHCID 71423726[4-Bromo-2-(propan-2-yl)phenyl]cyanamide

Product 1

HCID 16037642[4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-isopropylphenyl]cyanamideYield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-bromo-2-isopropylphenylcyanamide (0.132 g, 0.5 mmol) tris (dibenzylideneacetone) dipalladium (11.6 mg, 0.0126 mmol), N-methyl-5-cyanopyrroleboronic acid (0.150 g, 1 mmol), and potassium carbonate (0.276 g, 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 (2 mL) was added with stirring. Then tri-tert-butylphosphine (0.0486 mL, 0.0252 mmol) was added to the mixture and allowed to stir until starting bromide was consumed. The mixture was then diluted with 1/1 hexane/ethylacetate and filtered through a plug of silica gel, solvent evaporated and the residue was flash chromatographed using 4/1 Hexane/THF to give (0.025 g, 18%) [4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-2-isopropylphenyl]cyanamide.

Workup

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

Sources & evidence

ORD record
ord-68d23c0b930c445a8fc8a86928270dac
Source dataset
uspto-grants-2007_11
Patent number
US07297713B2

Reaction notes

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