Ethanol → N-(5-Bromopyridin-3-yl)-4-methylbenzene-1-sulfonamide

HRID 2077552Notes

Reaction equation

HRID 2077552 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(O)C.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:12])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 73974-Toluenesulfonyl chlorideHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 57585105N-(5-Bromopyridin-3-yl)-4-methylbenzene-1-sulfonamide

Procedure

To a round-bottom flask charged with 5-bromopyridin-3-amine (0.400 g, 2.3 mmol) in ethanol (10 ml, 171 mmol), was added 4-methylbenzene-1-sulfonyl chloride (0.880 g, 4.6 mmol) into the mixture. The mixture was allowed to stir at ambient temperature overnight, while under inert atmosphere. 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 10-30% EtOAc/DCM. The fractions with desired product were combined and concentrated. This gave N-(5-bromopyridin-3-yl)-4-methylbenzenesulfonamide (0.350 g, 46% yield) as a light-yellow crystalline solid. MS (ESI pos. ion) m/z: 328 (MH+). Calc'd exact mass for Cl2H, BrN2O2S: 327. 1H NMR (400 MHz, chloroform-d): 2.43 (d, J=18.57 Hz, 3H), 7.35 (d, J=6.53 Hz, 2H), 7.69 (d, J=6.02 Hz, 2H), 7.80 (d, J=5.02 Hz, 2H), 8.13-8.20 (m, 1H), 8.42 (s, 1H).

Sources & evidence

ORD record
ord-c83814092d3b4f0c99bfee14aae1d978
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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