7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole synthesis
- Product Name:7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole
- CAS Number:1326714-48-0
- Molecular formula:C13H16BNO2S
- Molecular Weight:261.15
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Yield:1326714-48-0 82%
Reaction Conditions:
with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in 1,4-dioxane at 90; for 3 h;
Steps:
Intermediate 60: 7-(4A5,5-tetramethyl-1 .S^-dioxaborolan^-vO-l ,3-benzothiazoleA mixture of 7-bromobenzothiazole (100.0 mg, 0.4671 mmol), bis(pinacolato)diboron(142 mg, 0.558 mmol), (1 , 1 'bis-(diphenylphosphino)-ferrocene) palladium dichloride (17.1 mg, 0.0234 mmol), and potassium acetate (80.0 mg, 0.815 mmol) in 1 ,4-dioxane (4 mL) was heated to 90 °C for 3 h. The solution was concentrated in vacuo and purified by column chromatography (3 to 5% EtOAc:heptane) to afford 100 mg (82%) the title compound as a white solid. 1 H NMR (400 MHz, CDCI3): δ 1.42 (s, 12 H), 7.56 (dd, J=8.1 , 7.1 Hz, 1 H), 7.89 - 7.97 (m, 1 H), 8.26 (dd, J=8.2, 1 .1 Hz, 1 H), 9.08 (s, 1 H); MS (ESI): 262.10 [M+H]+; H PLC tR = 1.59 min (TOF: polar_3min).
References:
WO2011/100502,2011,A1 Location in patent:Page/Page column 50
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