5-(Methylsulfonyl)pyridine-3-boronic acid pinacol ester → 1-{5-Chloro-4-fluoro-2-hydroxy-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethanone

HRID 511036Notes

Reaction equation

HRID 511036 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[C:4](I)[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH3:14][S:15]([C:18]1[CH:19]=[N:20][CH:21]=[C:22](B2OC(C)(C)C(C)(C)O2)[CH:23]=1)(=[O:17])=[O:16]>>[Cl:1][C:2]1[C:3]([F:13])=[C:4]([C:22]2[CH:21]=[N:20][CH:19]=[C:18]([S:15]([CH3:14])(=[O:17])=[O:16])[CH:23]=2)[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

3

Reactant 2

HCID 533985305-(Methylsulfonyl)pyridine-3-boronic acid pinacol esterHCID 866668571-(5-Chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone

Product 1

HCID 866669571-{5-Chloro-4-fluoro-2-hydroxy-3-[5-(methylsulfonyl)pyridin-3-yl]phenyl}ethanoneYield 87%

Procedure

The desired compound was prepared according to the procedure of Example 127, step A, using 1-(5-chloro-4-fluoro-2-hydroxy-3-iodophenyl)ethanone (See, Example 172, Step 2) and 3-(methylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (PepTech Corp., Cat. No. BE358) as the starting materials in 87% yield. LCMS for C14H12ClFNO4S (M+H)+: m/z=344.0. Found: 343.9.

Sources & evidence

ORD record
ord-9038cf1a7bbb4767a6c1fc4888b59fb8
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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