4-Methoxybenzenesulfonyl chloride → 4-Methoxy-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

HRID 1052377Notes

Reaction equation

HRID 1052377 reaction equation
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:9][C:8]2[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([B:10]3[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]3)[CH:7]=2)(=[O:29])=[O:28])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

Product 1

HCID 899608284-Methoxy-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamideYield 80.3%

Procedure

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine (200 mg, 0.8 mmol) was treated with 4-methoxybenzene-1-sulfonyl chloride (331 mg, 1.6 mmol) according to the method of Preparation 15b to give 270 mg (77% yield) of the title compound as an oil. Purity 96%.

Sources & evidence

ORD record
ord-0e565b7b614b48c5b1ec305eb4776480
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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