Bromide ion → HCID 16037646, compound

HRID 1993969Notes

Reaction equation

HRID 1993969 reaction equation
[N:1]#[C:2][NH2:3].[CH3:4][N:5]1[C:9]([C:10]#[N:11])=[CH:8][CH:7]=[C:6]1B(O)O.C(=O)([O-])[O-].[K+].[K+].C(P([C:30]([CH3:33])([CH3:32])C)C(C)(C)C)(C)(C)C.[Br-].[CH2:35]1[CH2:39][O:38][CH2:37][CH2:36]1>>[C:10]([C:9]1[N:5]([CH3:4])[C:6]([C:32]2[CH:30]=[CH:33][C:35]([NH:1][C:2]#[N:3])=[CH:36][C:37]=2[O:38][CH3:39])=[CH:7][CH:8]=1)#[N:11]

Participants

7

Reactant 6

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 9864CyanamideHCID 11430Potassium CarbonateHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 11708078(5-cyano-1-methyl-1H-pyrrol-2-yl)boronic acid

Product 1

HCID 16037646HCID 16037646, compoundYield 16%

Procedure

4-bromo-3-methoxyphenyl)cyanamide (0.113 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. Tri-tert-butylphosphine (10 wt % in hexane) (0.0486 mL, 0.0252 mmol) was added to the mixture and allowed to stir until the starting bromide was consumed. The mixture was then diluted with 1/1 hexane/ethylacetate, filtered through a plug of silica gel, solvent evaporated and the residue was flash chromatographed on silica gel using 4/1 Hexane/THF to give [4-(5-cyano-1-methyl-1H-pyrrol-2-yl)-3-methoxyphenyl]cyanamide (0.020 g, 16%).

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, solvent
  6. customevaporated
  7. customchromatographed on silica gel using 4/1 Hexane/THF

Sources & evidence

ORD record
ord-abf31ccf07b94f20a3b84cda2b50c4fa
Source dataset
uspto-grants-2010_01
Patent number
US07652062B2

Reaction notes

Loading…