1,3-BENZOTHIAZOL-6-YLBORONIC ACID,97%
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1,3-BENZOTHIAZOL-6-YLBORONIC ACID,97%
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CAS No:
499769-91-4
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Formula:
C7H6BNO2S
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Chemical Name:
1,3-BENZOTHIAZOL-6-YLBORONIC ACID,97%
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Synonyms:
1,3-Benzothiazol-6-ylboronic acid;1,3-BENZOTHIAZOL-6-YLBORONIC ACID,97%;Boronic acid, 6-benzothiazolyl- (9CI);Benzo[d]thiazol-6-ylboronic acid
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CAS No:
1,3-BENZOTHIAZOL-6-YLBORONIC ACID,97% Use and Manufacturing
General procedure: To a solu of 14 (60 mg, 0.14 mmol) in DMF (2 mL) was added selected aryl boronic acid (0.22 mmol) and 2 M Na2CO3 (0.2 mL). The reaction mixture was degassed with bubbling N2 (g) for 10 mins. Added PdCl2(dppf) (10 mg, 0.013 mmol), heated to 60 C and stirred for 10-30 mins. The reaction was cooled to room temperature, diluted with 5% LiCl (aq. Solu., 16 mL) and extracted with EtOAc (2 x 10 mL). The combined organic extracts were washed with 5% LiCl (aq. Solu., 2 x 15 mL) and brine (20 mL), dried over Na2SO4, passed through a plug of celite and concentrated under vacuum. The residue was purified by column chromatography using 0 to 100% EtOAc in hexanes then 0 to 10% MeOH in EtOAc to afford the desired product:To a solution of 5-bromo-6-chloropyrazin-2-amine (0.600 g, 2.8 mmol, 1 eq.) and To a stirred solution of 5-bromo-6-phenylpyrazin-2-amine (0.500 g, 2.0 mmol, 1.0 eq.) and To a solution of 6-bromo-7-phenyl-1, 8-naphthyridin-4(1H)-one (100 mg, 0.40 mmol, 1 eq.) in dioxane-water (10 mL) was added To a solution of 6-bromo-7-(5-methylfuran-2-yl)-1, 8-naphthyridin-4(1H)-one (100 mg, 0.33 mmol, 1 eq.) in 1, 4 dioxane (8 mL): water (2 mL) was added General procedure: A glass microwave vesselwas chargedwith compound 60 (40 mg, 0.128mmol), 4-(hydroxymethyl)phenylboronic acid (29 mg, 0.192mmol), sodium carbonate (41 mg, 0.384 mmol), and dioxane/water (1.0mL:0.18 mL). The solution was purged with nitrogen for5 min, then Pd(PPh3)4 (15mg, 0.013 mmol) was added. The reactionmixture was stirred and heated at 120 C for 64 h. The reactionmixturewas filtered and washed with EtOAc/MeOH. The was concentratedand purified by reverse phase HPLC to give 21 mg (43%) ofthe title compound as an amorphous solid.
Computed Properties
Molecular Weight:179.01
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:179.0212298
Monoisotopic Mass:179.0212298
Topological Polar Surface Area:81.6
Heavy Atom Count:12
Complexity:170
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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