Pyridine → HCID 71257318, compound

HRID 710095Notes

Reaction equation

HRID 710095 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:3]=1[NH2:4].N1C=CC=CC=1.[F:16][C:17]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:23]=[CH:22][C:18]=1[C:19](Cl)=[O:20]>C(Cl)Cl.O>[Br:1][C:2]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:3]=1[NH:4][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:24]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:25][C:17]=1[F:16]

Participants

6

Reactant 3

HCID 1049PyridineHCID 771982,5-DibromoanilineHCID 189779422-Fluoro-4-(methylsulfonyl)benzoyl chloride

Product 1

HCID 71257318HCID 71257318, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-4-(methylsulfonyl)benzoic acid (1 g, 4.6 mmol) dissolved in DCM (15 ml), cooled to 0° C. and added oxalyl chloride (0.6 ml, 6.9 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 2-fluoro-4-(methylsulfonyl)benzoyl chloride quantitatively. 2,5-Dibromoaniline (0.9 g, 3.59 mmol) dissolved in DCM (10 ml) and added Pyridine (0.34 g, 4.30 mmol) under nitrogen atmosphere. This mixture stirred at rt for 30 mins and added 2-fluoro-4-(methylsulfonyl)benzoyl chloride (1.01 g, 3.59 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 (1.6 g) as a brown solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 10.34 (s, 1H), 8.34-7.99 (m, 1H), 7.98-7.93 (m, 2H), 7.92-7.89 (m, 1H), 7.68 (d, J 8.6, 1H), 7.43 (dd, J 2.4, 8.6, 1H), 3.33 (s, 3H).

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-0762639029284be79bfa41b4d92bf377
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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