2-Propanol, 1-[[4-aMino-2-[3,3-diMethyl-4-(phenylMethoxy)-1-butyn-1-yl]-5-fluorophenyl]aMino]-3-(phenylMethoxy)-, (2R)- synthesis

11synthesis methods

Product Name:2-Propanol, 1-[[4-aMino-2-[3,3-diMethyl-4-(phenylMethoxy)-1-butyn-1-yl]-5-fluorophenyl]aMino]-3-(phenylMethoxy)-, (2R)-
CAS Number:1294504-66-7
Molecular formula:C29H33FN2O3
Molecular Weight:476.58

Benzene, [[(2,2-diMethyl-3-butyn-1-yl)oxy]Methyl]-

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1294504-64-5 Synthesis

(R)-4-((3-(benzyloxy)-2-hydroxypropyl)amino)-5-bromo-2-fluorobenzenaminium4-methylbenzenesulfonate

1294504-64-5
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2-Propanol, 1-[[4-aMino-2-[3,3-diMethyl-4-(phenylMethoxy)-1-butyn-1-yl]-5-fluorophenyl]aMino]-3-(phenylMethoxy)-, (2R)-

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Yield:1294504-66-7 86%

Reaction Conditions:

with palladium diacetate;potassium carbonate;1,4-di(diphenylphosphino)-butane in acetonitrile at 80; for 16 h;Inert atmosphere;

Steps:

1.16 Step 16

Step 16[00172] (R)-l-(4-amino-2-(4-(benzyloxy)-3.3-dimethylbut-l-vnyl)-5-fluorophenylamino)- 3-(benzyloxy)propan-2-ol: To a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 4-[[(2R)-3-(benzyloxy)-2-hydroxypropyl]amino]-5- bromo-2-fluoroanilinium 4-methylbenzene-l -sulfonate (2.9 g, 5.36 mmol, 1.00 equiv.), [[(2,2-dimethylbut-3-yn-l-yl)oxy]methyl]benzene (1.2 g, 6.37 mmol, 1.20 equiv.), Pd(OAc)2 (48 mg, 0.21 mmol, 0.04 equiv.), dppb (138 mg, 0.32 mmol, 0.06 equiv.), potassium carbonate (2.2 g, 15.92 mmol, 3.00 equiv.) and MeCN (50 mL). The resulting solution was stirred for 16 h at 80 °C. The solids were filtered out and the resulting mixture was concentrated under vacuum until LCMS indicated the completion of the reaction. The residue was purified by a silica gel column, eluted with ethyl acetate/petroleum ether (1 :4) to afford 2.2 g (86%) of l-N-[(2R)-3-(benzyloxy)-2-hydroxypropyl]-2-[4-(benzyloxy)-3,3- dimethylbut-l-yn-l-yl]-5-fluorobenzene-l ,4-diamine as a light brown solid.

References:

WO2016/109362,2016,A1 Location in patent:Paragraph 00172

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