Cesium carbonate → HCID 24822921, compound

HRID 273535Notes

Reaction equation

HRID 273535 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:20]=[C:19]([CH3:21])[C:13]2[N:14]=[C:15]([NH2:18])[N:16]=[N:17][C:12]=2[CH:11]=1.[CH2:22]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([S:38]([C:41]2[CH:46]=[CH:45][C:44](Br)=[CH:43][CH:42]=2)(=[O:40])=[O:39])[CH2:34][CH2:33]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[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>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH2:22]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([S:38]([C:41]2[CH:46]=[CH:45][C:44]([NH:18][C:15]3[N:16]=[N:17][C:12]4[CH:11]=[C:10]([C:3]5[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=5[Cl:1])[CH:20]=[C:19]([CH3:21])[C:13]=4[N:14]=3)=[CH:43][CH:42]=2)(=[O:39])=[O:40])[CH2:34][CH2:33]1)=[O:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 248227537-(2-Chloro-5-methoxyphenyl)-5-methylbenzo[e][1,2,4]triazin-3-amineHCID 59837669HCID 59837669, compound

Product 1

HCID 24822921HCID 24822921, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst

Procedure

In a dry 25 mL round bottom flask, 7-(2-chloro-5-methoxy-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine (0.132 g, 0.44 mmol, 1 equiv), 4-(4-bromo-benzenesulfonyl)-piperidine-1-carboxylic acid benzyl ester (0.232 g, 0.529 mmol, 1.2 equiv), Cesium carbonate (0.432 g, 1.33 mmol, 3 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (0.051 g, 0.088 mmol, 0.2 equiv) and tris(dibenzylideneacetone) dipalladium (0.040 g, 0.044 mmol, 0.1 equiv) were combined. The reactants were flushed with argon, diluted with dioxane (12 mL) and outfitted with a reflux condenser. The reaction was heated to reflux for 18 hours, then cooled to room temperature and slowly diluted with water. The resulting precipitate was collected and dried yielding a yellow powder (0.271 g, 93% yield). MS (ESI+): m/z=658.2, LC retention time: 3.41 min.

Workup

  1. customThe reactants were flushed with argon
  2. additiondiluted with dioxane (12 mL)
  3. customoutfitted with a reflux condenser
  4. temperatureThe reaction was heated
  5. temperatureto reflux for 18 hours
  6. additionslowly diluted with water
  7. customThe resulting precipitate was collected
  8. customdried

Sources & evidence

ORD record
ord-16418fa0dd8e48f899d2532bf9ade07e
Source dataset
uspto-grants-2008_11
Patent number
US07456176B2

Reaction notes

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