1-BROMO-5-METHYLHEXANE

1-bromo-5-methyl-hexane (25); To a stirred solution of LiBr (6.26 g; 72.0 mmol) in DMF (40 mL) a solution of 24 (6.60 g; 24.4 mmol) in DMF (6 mL) was added. The resulting mixture was stirred at 45° C. for 3 h. Then water (100 mL) was added and the reaction product was extracted with diethyl ether (5.x.250 mL). Removal of solvent yielded in 2.40 g (13.4 mmol; 55percent) of 25. To a stirred solution of LiBr (6.26 g; 72.0 mmol) in DMF (40 mL) a solution of 23 (6.60 g; 24.4 mmol) in DMF (6 mL) was added. The resulting mixture was stirred at 45° C. for 3 h. Then water (100 mL) was added and the reaction product was extracted with diethyl ether (5.x.250 mL). Removal of solvent yielded in 2.40 g (13.4 mmol; 55percent) of 24. 1-Bromo-5-methyl-hexane (19); To a stirred solution of LiBr (6.26 g; 72.0 mmol) in DMF (40 mL) a solution of 18 (6.60 g; 24.4 mmol) in DMF (6 mL) was added. The resulting mixture was stirred at 45° C. for 3 h. Then water (100 mL) was added and the reaction product was extracted with diethyl ether (5.x.250 mL). Removal of solvent yielded in 2.40 g (13.4 mmol; 55percent) of 19. 1-bromo-5-methyl-hexane (20).; To a stirred solution of LiBr (6.26 g; 72.0 mmol) in DMF (40 mL) a solution of 19 (6.60 g; 24.4 mmol) in DMF (6 mL) was added. The resulting mixture was stirred at 45° C. for 3 h. Then water (100 mL) was added and the reaction product was extracted with diethyl ether (5.x.250 mL). Removal of solvent yielded in 2.40 g (13.4 mmol; 55percent) of 20. B. Preparation of 2-methyloctadecine-(7) by brief reaction with sodium in liquid ammonia, addition of dodecine-(1) and (5-methylhexyl)triphenylphosphonium bromide (10) A solution of 25 (2.30 g; 12.8 mmol) and triphenylphosphine (3.70 g; 14.1 mmol) was refluxed in toluene (12 mL) for 20 h. Then solvent was removed and the resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL) to give 4.57 g (10.4 mmol; 81% yield) of 10. m.p. 227-228 C.; 1H NMR (500 MHz, CD3CN) delta 0.82 (6H, d, J=6.6 Hz), 1.16 (2H, m), 1.42-1.52 (3H, m), 1.59 (2H, m), 3.30 (2H, m), 7.72 (12H, m), 7.85 (3H, m); 13C NMR (125 MHz, CD3CN) delta 22.7, 23.2, 28.4, 28.8, 28.9, 38.6, 131.2, 131.3, 134.7, 134.7, 136.0.(5-methylhexyl)triphenylphosphonium bromide (10) A solution of 19 (2.30 g; 12.8 mmol) and triphenylphosphine (3.70 g; 14.1 mmol) was refluxed in toluene (12 mL) for 20 h. Then solvent was removed and the resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL) to give 4.57 g (10.4 mmol; 81% yield) of 10. m.p. 227-228 C.; 1H NMR (500 MHz, CD3CN) delta 0.82 (6H, d, J=6.6 Hz), 1.16 (2H, m), 1.42-1.52 (3H, m), 1.59 (2H, m), 3.30 (2H, m), 7.72 (12H, m), 7.85 (3H, m); 13C NMR (125 MHz, CD3CN) delta 22.7, 23.2, 28.4, 28.8, 28.9, 38.6, 131.2, 131.3, 134.7, 134.7, 136.0.A solution of 24 (2.30 g; 12.8 mmol) and triphenylphosphine (3.70 g; 14.1 mmol) was refluxed in toluene (12 mL) for 20 h. Then solvent was removed and the resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL) to give 4.57 g (10.4 mmol; 81% yield) of 10. m.p. 227-228 C.; 1H NMR (500 MHz, CD3CN) delta 0.82 (6H, d, J=6.6 Hz), 1.16 (2H, m), 1.42-1.52 (3H, m), 1.59 (2H, m), 3.30 (2H, m), 7.72 (12H, m), 7.85 (3H, m); 13C NMR (125 MHz, CD3CN) delta 22.7, 23.2, 28.4, 28.8, 28.9, 38.6, 131.2, 131.3, 134.7, 134.7, 136.0.(5-methylhexyl)triphenylphosphonium bromide (10). A solution of 20 (2.30 g; 12.8 mmol) and triphenylphosphine (3.70 g; 14.1 mmol) was refluxed in toluene (12 mL) for 20 h. Then solvent was removed and the resulting crystal was washed with toluene (3 mL) and diethyl ether (3 mL) to give 4.57 g (10.4 mmol; 81% yield) of 10. m.p. 227÷228 C.; 1H NMR (500 MHz, CD3CN) delta 0.82 (6H, d, J=6.6 Hz), 1.16 (2H, m), 1.42-1.52 (3H, m), 1.59 (2H, m), 3.30 (2H, m), 7.72 (12H, m), 7.85 (3H, m); 13C NMR (125 MHz, CD3CN) delta 22.7, 23.2, 28.4, 28.8, 28.9, 38.6, 131.2, 131.3, 134.7, 134.7, 136.0.[007171 Prepared using General Procedure 12 from tert-butyl ()-3-(2-(4-(tert- butyl)benzamido)-3 -(4-(5-(4-hydroxyphenyl)pyrirnidin-2-vl)phenyl)propanamido)propanoate and 1 -brorno-5-methyl hexane. LCMS-ESI (ni/z) calculated for C44H56N405: 720.9; found 721.4 [M+Hj. 1R = 5.39 mm. (Method 16).

Molecular Weight:179.10
XLogP3:3.6
Rotatable Bond Count:4
Exact Mass:178.03571
Monoisotopic Mass:178.03571
Heavy Atom Count:8
Complexity:41.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes