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?. Suzuki and . Miyaura-cross-coupling-reaction, General procedure A glass tube was loaded with 2-bromophenyltetrazole (68 mg, 0.3 mmol), the appropriate arylboronic acid (0.6 mmol, Na 2 CO 3 (48 mg, 0.45 mmol), PdCl 2 (dppf) (24.5 mg, 0.03 mmol), DME (1.5 mL) and H 2 O (0.6 mL)

1. , J. Hh-=-1h, and J. Hh, The mixture was diluted with NaHCO 3 (5%) and ethyl acetate (10 ml) The organic layer was extracted with NaHCO 3 (5%) (4 · 20 mL) and aqueous layers were combined, washed with ethyl acetate (5 mL), acidified (pH = 1) and extracted with ethyl acetate (5 · 30 mL) The combined organic layers were dried (MgSO 4 ) The solvent was removed in vacuo. 5-(3 0 -Methoxy-biphenyl-2-yl)-1H-tetrazole (3a): Yield: 58%, pale yellow oil, 1 H NMR (300 MHz, DMSO-d 6 ): d = 730 (s, 3H, OCH 3 ), After one vacuum/Argon cycle to remove oxygen, the reaction tube was sealed; the mixture was stirred and heated at 115 °C in microwave oven for 30 min C NMR (75 MHz LCMS (EI1H-Tetrazol-5-yl)-biphenyl-4-yl]-methanol, pp.4399531-4399534

1. , J. Ch-=-7dd, 1. , and J. Ch, DMSOd 6 ): d = 7.69 (m, 2H, Harom)58 (m, 2H, Harom), Yield: 55%, colourless oil, 1 H NMR (300 MHz67 (s, 2H, CH 2 OH), 13 C NMR (75 MHz, DMSO-d 6 ): d = 131, p.2063

6. Harom-)-d, 2. , and J. Ch, Harom); 13 C NMR (75 MHz, DMSO-d 6 ): d = 131, Yield: 55%, pale yellow oil, 1 H NMR (300 MHz LCMS (EI): m/z = 291, p.335

2. and J. Hh-=, 1H-tetrazole (3d): Yield: 57%, yellow oil, 1 H NMR (300 MHz, DMSO-d 6 ): d = 7.62 (m, 4H, Harom)33 (d 2H, J HH = 8.4 Hz, Harom), 26 (s, 9H, C(CH 3 ) 3 ), 13 C NMR (75 MHz LCMS (EI): m/z = 279, pp.7-31

2. Chm, 2. , and J. Ch, Yield: 55%, pale yellow solid mp: 162?164 °C, 1 H NMR (300 MHz, DMSO-d 6 ): d = 10.05 (s, 1H, CHO) DMSOd 6 ): d = 193, 13 C NMR (75 MHz LCMS (EI): m/z = 251, p.8533256

1. Chtd, 1. , J. Ch, 1. , and J. Ch, Yield: 58%, pale yellow solid; mp 128?129 °C, 1 H NMR (300 MHz, DMSO-d 6 ): d = 7.7 (m, 2H, Harom)58 (m, 2H, Harom), 86 (d, 1H, J CH = 7.5 Hz, Harom), 13 C NMR (75 MHz, pp.343-344

H. Nmr, 300 MHz, DMSO-d 6 ): d = 8

. Hz, 2. Harom-)-d, J. Hh-=-4t, 1. , and J. , 8 Hz, Harom); 13 C NMR (75 MHz, DMSO-d 6 ): d = 131, LCMS (EI): m/z = 238, p.303

H. Nmr, 84 (m, 4H, Harom); 13 C NMR (75 MHz, DMSO-d 6 ): d = 142, LCMS (EI): m/z = 224, p.323

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DOI : 10.1016/j.tetlet.2005.07.082
URL : https://hal.archives-ouvertes.fr/inserm-00110439