ChemicalBook CAS DataBase List 3-METHANESULFONYLAMINOPHENYLBORONIC ACID, PINACOL ESTER

3-METHANESULFONYLAMINOPHENYLBORONIC ACID, PINACOL ESTER synthesis

5synthesis methods

Product Name:3-METHANESULFONYLAMINOPHENYLBORONIC ACID, PINACOL ESTER
CAS Number:305448-92-4
Molecular formula:C13H20BNO4S
Molecular Weight:297.18

83922-51-4 Synthesis

83922-51-4
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73183-34-3
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3-METHANESULFONYLAMINOPHENYLBORONIC ACID, PINACOL ESTER

305448-92-4
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$39.00/250mg

Yield: 94.8%

Reaction Conditions:

Stage #1:3-(methylsulfonyl)amino-1-bromo-benzene;bis(pinacol)diborane in 1,2-dimethoxyethane for 0.166667 h;Inert atmosphere;
Stage #2: with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,2-dimethoxyethane at 80;Inert atmosphere;

Steps:

Step-ii: N -(3-( 4.4.5 .5-tetramethyl-1 .3 .2-dioxaborolan-2-yl)phenyl)methanesulfonamide
Step-ii: N -(3-( 4.4.5 .5-tetramethyl-1 .3 .2-dioxaborolan-2-yl)phenyl)methanesulfonamide15 N-(3-bromophenyl) methane sulfonamide (8.3 g, 33 mmol) and bispinocalatodiboron (10.11g, 39.8 mmol) were added to a solution of DME (80 ml) previously purged with argon (10min). The reaction mixture was purged with argon for a further 15mins, followed by theaddition of potassium acetate (9.77 g, 94.6 mmol) and PdClz(dppf) (813 mg, 0.99 mmol). Theresulting mixture was heated to reflux at 80 oc overnight. The reaction was monitored by20 TLC (15% ethyl acetate in hexane). The reaction mixture was cooled and diluted with ethylacetate (100 ml) and filtered over celite bed and the filtrate was washed with water (2x100ml). The organic layer was dried over Na2S04, and concentrated under reduced pressure toafford the crude product. Purification by column chromatography on silica gel (15% ethylacetate in hexane) afforded 9.3 g (94.8% yield) of N-(3-(4,4,5,5-tetramethyl-1,3,2-25 dioxaborolan-2-yl)phenyl) methane sulfonamide. MS: m/z = 298.1 (M+l).

References:

AURIGENE DISCOVERY TECHNOLOGIES LIMITED;UM PHARMAUJI SDN. BHD;GUMMADI, Venkateshwar, Rao;HOSAHALLI, Subramanya;NANDURI, Srinivas;AGGUNDA RENUKAPPA, Girish WO2014/6554, 2014, A1 Location in patent:Page/Page column 28