Nitrogen → N-(5-Bromo-2-chloro-3-pyridinyl)-4-(1-hydroxy-1-methylethyl)benzenesulfonamide

HRID 1162474Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:15]([Cl:21])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:22][Mg]Br.N#N>C1COCC1>[Br:20][C:18]1[CH:19]=[C:14]([NH:13][S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])([CH3:22])[CH3:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[C:15]([Cl:21])=[N:16][CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a 100 mL, round-bottomed flask was added 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide from Step 1 (250 mg, 642 μmol) and THF (10 mL). To this solution, methylmagnesium bromide (3.0 N, 4 mL, 12 mmol) was added in under N2 protection. The suspension was stirred at 25° C. for 3 h. The mixture was quenched by aqueous saturated NH4Cl. The aqueous part was extracted by 10% methanol-DCM (3×), and the combined organic was dried over MgSO4, and concentrated in vacuo to provide the title product as a yellow oil (250 mg), which was taken on to the next step without further purification. MS (ESI positive ion) m/z: 407 (M+1).

Workup

customThe mixture was quenched by aqueous saturated NH4Cl
extractionThe aqueous part was extracted by 10% methanol-DCM (3×)
dry with materialthe combined organic was dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6a4066f6c51341f8af681ccf53cdb54f
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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