3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5- (tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2- aMine synthesis

10synthesis methods

Product Name:3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5- (tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2- aMine
CAS Number:877399-08-1
Molecular formula:C19H22BCl2FN2O3
Molecular Weight:427.11

Imidodicarbonic acid, 2-[3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]-, 1,3-bis(1,1-dimethylethyl) ester

1331786-34-5
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3-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-
(tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-
aMine

877399-08-1
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Yield:877399-08-1 100%

Reaction Conditions:

with hydrogenchloride in 1,4-dioxane;dichloromethane at 0 - 40; for 26 h;

Steps:

1.7 Step 7 (±)-3-(1 -(2,6-dichloro-3-fluoropheny)ethoxy)-5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-amine

Step 7 (±)-3-(1 -(2,6-dichloro-3-fluoropheny)ethoxy)-5-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-amine [00176] To a solution of (±)-bis(Boc) protected 3-(1 -(2,6-dichloro-3- fluoropheny)ethoxy)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-2-amine (3.83 g, 6.1 mmol) in DCM (15 mL) was added a solution of HCI in dioxane (4.0 N, 7.6 mL). The solution was stirred at room temperature for 18 hrs and 40 °C for 8 hrs. The solution was concentrated to give the residue which was dissolved in EtOAc (180 mL). The solution was washed with saturated NaHCO3 solution (2x50 mL), brine (50 mL), dried over anhydrous Na2SO4, and then concentrated by evaporator in vacuo to afford (±)-3-(1 -(2,6-dichloro-3-fluoropheny)ethoxy)-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl)pyridin-2-amine (2.6 g , 100%) as a pale yellow solid. [00177] 1HNMR (300 MHz, CDCI3): δ 8.01 (s, 1 H), 7.27 (dd, 1 H), 7.17 (s, 1 H), 7.06 (t, 1 H), 6.12 (q, 1 H), 5.02 (s, br, 2 H), 1 .81 (d, 3 H), 1 .30 (s, 6 H), 1 .28 (s, 6 H).

References:

WO2013/13308,2013,A1 Location in patent:Paragraph 00175-00177

756503-69-2 Synthesis