ChemicalBook CAS DataBase List 6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine synthesis

9synthesis methods

Product Name:6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine
CAS Number:1403903-11-6
Molecular formula:C16H17FN2
Molecular Weight:256.32

6-chloro-2,3-dihydro-3,3-dimethyl-1H-Pyrrolo[3,2-b]pyridine

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312693-07-5
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6-(4-fluorobenzyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

1403903-11-6
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Yield:1403903-11-6 81.2%

Reaction Conditions:

with palladium diacetate;lithium bromide;dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane in tetrahydrofuran;1-methyl-pyrrolidin-2-one at 30 - 36; for 12 h;

Steps:

3A Example 3A: Preparation and synthesis of the compound of formula (VII):

Lithium bromide (71.32 g, 3.0 eq), palladium acetate (0.614 g, 0.01 eq) and XPhos (3.39 g, 0.026 eq) were added to a solution of the compound of formula (V) (50 g, 1 eq) in N- methyl- pyrrolidone (100 mL) and tetrahydrofuran (150 mL). The reaction mixture was heated to a temperature of 30 to 36°C, and 4-fluorobenzyl zinc chloride (821 mL, 1.5 eq, 0.5 M in THF) was added. The reaction mixture was heated to a temperature of 30-36°C for 12 hours. Upon reaction completion, the reaction mixture was cooled to a temperature of 15 to 25°C and quenched with a 13% aqueous solution of ammonium chloride (220 mL). The reaction mixture was filtered, and the aqueous phase was extracted with toluene (250 mL). The combined organic layer was concentrated to about 1.05 L volume and washed twice with a 13% aqueous solution of ammonium chloride (220 mL) at a temperature of 45 to 55°C. The organic layer was concentrated to about 200 mL volume and cooled to a temperature of 15 to 25°C. Heptane (500 mL) was added and stirred at a temperature of 15 to 25°C for 30 min, filtered and washed with heptane (100 mL). The solid was dried under vacuum to a temperature of 40°C for about 8 to 10 hours to obtain the compound of the formula (VII) (68.5 g, 81.2% yield, 98.5% area HPLC purity).

References:

WO2021/225955,2021,A1 Location in patent:Paragraph 0312

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References