Pyridine → HCID 71257595, compound

HRID 710108Notes

Reaction equation

HRID 710108 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[OH:9].N1C=CC=CC=1.[F:16][C:17]([F:28])([F:27])[C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([C:17]([F:16])([F:27])[F:28])=[CH:19][CH:20]=2)=[C:3]([OH:9])[CH:4]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 143206052-Amino-5-bromophenol

Product 1

HCID 71257595HCID 71257595, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(Trifluoromethyl)benzoic acid (0.8 g, 4.2 mmol) dissolved in DCM (20 ml), cooled to 0° C. and added oxalyl chloride (0.8 g, 6.1 mmol). Catalytic amount of DMF was added to this mixture and stirred at rt for 30 mins. After 30 mins, DCM removed on rotavapour and co-distilled the residue two times with DCM to obtain 4-(trifluoromethyl)benzoyl chloride quantitatively. 2-Amino-5-bromophenol (0.71 g, 3.8 mmol) dissolved in DCM (20 ml) and added Pyridine (0.32 ml, 4.1 mmol) under nitrogen atmosphere. This mixture stirred at rt for 30 mins and added 4-(trifluoromethyl)benzoyl chloride (0.88 g, 4.2 mmol). After continuing stirring at rt for 15 mins, reaction mass diluted with water and extracted with DCM. DCM layer washed with aq. NaHCO3 and DCM removed on rotavapour to obtain the solid. Solid was triturated with Et2O and Petether mixture (4:1) to obtain the titled compound (0.6 g) as a yellow solid.

Workup

  1. stirringAfter continuing stirring at rt for 15 mins
  2. customreaction mass
  3. extractionextracted with DCM
  4. washDCM layer washed with aq. NaHCO3 and DCM
  5. customremoved on rotavapour
  6. customto obtain the solid
  7. customSolid was triturated with Et2O and Petether mixture (4:1)

Sources & evidence

ORD record
ord-1e60e3ebfde94c3db84d493b42670790
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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