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. 2021 Jul 20;22(14):7735. doi: 10.3390/ijms22147735

Scheme 2.

Scheme 2

Reagents and conditions: (i) Pd(PPh3)4, (EtO)2P(O)H, DIPEA, MeCN, 70 °C, 3 h, 78%; (ii) (a) TMS-Br, DCM, r.t., 32 h, (b) MeOH, r.t., 1 h, (c) KOH, THF/MeOH, r.t., 1 h, 25%; (iii) Mo(CO)6, Pd(OAc)2, dppp, Et3N, DMSO/MeOH (3:2), 70 °C, 20 h, 40% (6), 48% (7); (iv) 2M LiOH (aq.), THF, 45 °C, 1 h, 71%; (v) 7M NH3 (MeOH), 50 °C, 4 d, 21%; (vi) 2-aminoethanol, K2CO3, EtOH, 50 °C, 24 h, 23%; (vii) a) DPPA, Et3N, DMF, 100 °C, 16 h, b) H2O, DMF, 100 °C, 3 h, 30%; (viii) AcOSu, Et3N, DMF, r.t., 36 h, 23%; (ix) Zn(CN)2, XantPhos Pd G2, DIPEA, DMF, 85 °C, 24 h, 61%; (x) NaN3, AcOH, DMF, 130 °C, 3h, 38%; (xi) 2M LiOH (aq.), THF, r.t., 24 h, 46%; (xii) potassium [[(t-butoxy-carbonyl)amino]methyl]trifluoroborate, SPhos Pd G2, K2CO3, THF/H2O (25:1), 100 °C, 2 h, 43%; (xiii) TFA, THF/H2O (4:1), 50 °C, 48 h, 73%.