Cesium carbonate → 4-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-yl amino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide

HRID 273527

Reaction equation

HRID 273527 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH2:12])[N:10]=[N:11][C:6]=2[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:3]=1.Br[C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:32][CH2:33][CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)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]>[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([NH:12][C:23]3[CH:28]=[CH:27][C:26]([S:29]([NH:32][CH2:33][CH2:34][N:35]4[CH2:36][CH2:37][CH2:38][CH2:39]4)(=[O:31])=[O:30])=[CH:25][CH:24]=3)[N:10]=[N:11][C:6]=2[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 40330904-Bromo-N-(2-(pyrrolidin-1-yl)ethyl)benzenesulfonamideHCID 598376075-Methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamine

Product 1

HCID 598376844-[5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-yl amino]-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamideYield 39%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

In a dry 25 mL round bottom flask, 5-methyl-7-(3-nitro-phenyl)-benzo[1,2,4]triazin-3-ylamine (0.223 g, 0.7935 mmol, 1 equiv), 4-bromo-N-(2-pyrrolidin-1-yl-ethyl)-benzenesulfonamide (0.396 g, 1.19 mmol, 1.5 equiv), cesium carbonate (0.776 g, 2.38 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.092 g, 0.159 mmol, 0.2 equiv) and tris(dibenzylideneacetone)dipalladium (0.073 g, 0.079 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (10 mL) and outfitted with a reflux condenser. The reaction was heated to reflux for 5 hours, then filtered hot and the solvents were evaporated. Silica gel column purification provided desired product as a yellow powder (0.16 g, 39% yield). MS (ESI+): m/z=582.1

Workup

  1. customThe reactants were flushed with argon
  2. additiondiluted with dioxane (10 mL)
  3. customoutfitted with a reflux condenser
  4. temperatureThe reaction was heated
  5. temperatureto reflux for 5 hours
  6. filtrationfiltered hot
  7. customthe solvents were evaporated
  8. customSilica gel column purification

Sources & evidence

ORD record
ord-e298ff2894a24f038612b2965fef1faa
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Linked notes

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