4-Bromoaniline → 8-(4-Bromo-phenylamino)-4-(2-chloro-phenyl)-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

HRID 2370623Notes

Reaction equation

HRID 2370623 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[N:12][C:13](S(C)=O)=[N:14][CH:15]=2)[N:10]2[CH:22]=[CH:23][N:24]=[C:9]12.[Br:25][C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.C([O-])(O)=O.[Na+]>>[Br:25][C:26]1[CH:32]=[CH:31][C:29]([NH:30][C:13]2[N:12]=[C:11]3[C:16]([C:17](=[O:18])[N:8]([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[Cl:1])[C:9]4[N:10]3[CH:22]=[CH:23][N:24]=4)=[CH:15][N:14]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 516892Sodium BicarbonateHCID 681947574-(2-Chloro-phenyl)-8-methanesulfinyl-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Product 1

HCID 681945998-(4-Bromo-phenylamino)-4-(2-chloro-phenyl)-4H-3,4,7,9,9b-pentaaza-cyclopenta[a]naphthalen-5-one

Procedure

A mixture of Example 1E (250.0 mg, 0.695 mmol) and 4-bromoaniline (191 mg, 1.112 mmol) was heated at 90° C. for 1 hour. While warm, the residue was treated with saturated aqueous NaHCO3 solution and extracted with ethyl acetate (twice). The combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was triturated with a small amount of ethyl acetate. The solids were filtered, washed with ethyl acetate/hexane, and oven-dried to provide the title compound.

Workup

  1. temperatureWhile warm
  2. extractionextracted with ethyl acetate (twice)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was triturated with a small amount of ethyl acetate
  7. filtrationThe solids were filtered
  8. washwashed with ethyl acetate/hexane
  9. customoven-dried

Sources & evidence

ORD record
ord-c05114562e6146aca6e5392d2ca33ab5
Source dataset
uspto-grants-2014_04
Patent number
US08710065B2

Reaction notes

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