1,2-Dimethoxyethane → N,N-diallyl-4-(3-(5-chloro-6-methoxypyridin-3-yl)phenylsulfonamido)pyridine-3-sulfonamide

HRID 2283343Notes

Reaction equation

[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[N:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[Cs+].[Cs+].COCCOC>Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH2:1]([N:4]([CH2:25][CH:26]=[CH2:27])[S:5]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:31]2[CH:32]=[N:33][C:34]([O:35][CH3:36])=[C:29]([Cl:28])[CH:30]=2)[CH:19]=1)(=[O:17])=[O:16])(=[O:7])=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N,N-diallyl-4-(3-bromophenylsulfonamido)pyridine-3-sulfonamide (0.29 g, 0.62 mmol), 5-chloro-6-methoxypyridin-3-ylboronic acid (0.15 g, 0.81 mmol), (1,1′-bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (0.026 g, 0.030 mmol), cesium carbonate (0.30 g, 0.93 mmol), 1,2-dimethoxyethane (4.5 mL) and water (0.5 mL) under an atmosphere of argon was heated at 100° C. for 15 min in a microwave reactor. The reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid, the organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using chloroform/methanol (98:2) as the eluent, gave the title compound in 58% yield.

Workup

customThe reaction mixture was partitioned between ethyl acetate and diluted hydrochloric acid
dry with materialthe organic phase was dried over magnesium sulfate
customthe solvent was evaporated
customPurification by column chromatography

Sources & evidence

ORD record: ord-fdc6b04dd0de4f7baf7ddd51aadebe30
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145380B2

Reaction notes

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