Trifluoroacetic acid → 7-amino-3-bromo-9H-carbazole-1-carboxamide

HRID 2410908Notes

Reaction equation

HRID 2410908 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([NH:18]C(=O)OC(C)(C)C)[CH:7]=[CH:6][C:5]2=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:18][C:8]1[CH:9]=[C:10]2[C:5]([C:4]3[CH:3]=[C:2]([Br:1])[CH:14]=[C:13]([C:15]([NH2:16])=[O:17])[C:12]=3[NH:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66605913tert-butyl 6-bromo-8-carbamoyl-9H-carbazol-2-ylcarbamate

Product 1

HCID 666051447-amino-3-bromo-9H-carbazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 6-bromo-8-carbamoyl-9H-carbazol-2-ylcarbamate (2.2 g, 5.44 mmol) was suspended into CH2Cl2 (30 mL). TFA (11 mL, 143 mmol) was added. The mixture was stirred for 1 hr at r.t. The mixture was concentrated to dryness. Saturated NaHCO3 water solution was added and stirred for 30 mins and filtered. The off white solid was collected and washed with water 2× and air-dried overnight to give the titled product. MS (ESI) m/z 303.95 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. additionSaturated NaHCO3 water solution was added
  3. stirringstirred for 30 mins
  4. filtrationfiltered
  5. customThe off white solid was collected
  6. washwashed with water 2×
  7. customair-dried overnight

Sources & evidence

ORD record
ord-770bd8b236e746d48c545e021e3b8570
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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