Pyridine → HCID 67097612, compound

HRID 2077559Notes

Reaction equation

HRID 2077559 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH3:9])[CH:5]=[N:6][CH:7]=1.[F:10][C:11]([F:23])([F:22])[C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.N1C=CC=CC=1>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:9])[S:18]([C:15]2[CH:14]=[CH:13][C:12]([C:11]([F:10])([F:22])[F:23])=[CH:17][CH:16]=2)(=[O:20])=[O:19])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 565998225-Bromo-N-methylpyridin-3-amine

Product 1

HCID 67097612HCID 67097612, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a microwave vial equipped with a stir bar and charged with 5-bromo-N-methylpyridin-3-amine (0.250 g, 1.3 mmol) in isopropanol (3 ml), was added 4-(trifluoromethyl)benzene-1-sulfonyl chloride (0.820 g, 3.3 mmol) and pyridine (0.32 ml, 4.0 mmol) into the mixture. The vial was capped and placed into a CEM Microwave for 20 minutes at 80° C., while 50 watts of energy was supplied via Powermax® (Simultaneous heating while cooling technology). The progress of the reaction was monitored by LC/MS, which showed mostly desired product. The mixture was diluted with DCM and saturated sodium bicarbonate solution, then extracted the organic layer with DCM (3×25 ml). The organics were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude was purified by ISCO silica-gel chromatography in a gradient of 0-5% isopropanol/DCM. The fractions with desired product were combined and concentrated in vacuo. This gave N-(5-bromopyridin-3-yl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide (0.300 g, 57% yield) as an off-white crystalline solid. MS (ESI pos. ion) m/z: 396 (MH+). Calc'd exact mass for C13H10BrF3N2O2S: 395. 1H NMR (400 MHz, DMSO-d6): 3.24 (s, 3H), 7.79 (s, 2H), 8.01 (s, 3H), 8.46 (s, 1H), 8.66 (s, 1H).

Workup

  1. customTo a microwave vial equipped with a stir bar
  2. customThe vial was capped
  3. temperaturewas supplied via Powermax® (Simultaneous heating while cooling technology)

Sources & evidence

ORD record
ord-246df0a1b67d4fa49a853875177145d2
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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