6-Bromonicotinic acid → HCID 87351673, compound

HRID 339529Notes

Reaction equation

HRID 339529 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=3[N:22]=2)=[CH:14][CH:13]=1>C1COCC1.CCOCC>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[S:19][C:20]4[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=4[N:22]=3)=[CH:16][CH:17]=2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 2389326-Bromonicotinic acidHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)aniline

Product 1

HCID 87351673HCID 87351673, compoundYield 29.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromonicotinic acid (0.16 g, 0.78 mmol) in dry THF (5 ml) was added under an atmosphere of argon 1,1′-carbonyldiimidazole (0.13 g, 0.78 mmol) and the reaction mixture stirred at room temperature for 5 h. To the reaction mixture was added 2-(4-aminophenyl)-6-methoxybenzothiazole (0.2 g, 0.78 mmol) over 2 mins, stirring continued at room temperature for 1 h, then heated under reflux for 18 h. After cooling to room temperature, the reaction mixture was diluted with Et2O (30 ml) and the precipitate was collected by filtration, washed with Et2O (50 ml) and dried under high vacuum to give the title compound (0.101 g, 29%) as an orange solid.

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 1 h
  3. temperatureheated
  4. temperatureunder reflux for 18 h
  5. temperatureAfter cooling to room temperature
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with Et2O (50 ml)
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-c52c3c14e8924b30877de7732b2128bf
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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