ChemicalBook CAS DataBase List Anastrozole

Anastrozole synthesis

10synthesis methods

Product Name:Anastrozole
CAS Number:120511-73-1
Molecular formula:C17H19N5
Molecular Weight:293.37

synthesis of anastrozole can be realized in four steps based on 3,5-bis(bromomethyl)toluene. Starting with a S N 2 displacement using potassium nitrile and tetrabutylammonium bromide as a phase transfer catalyst to give bis-nitrile compound. Bis-nitrile compound formed undergoes deprotonation with NaH and methylated afterwards with methyl iodide to give bis-dimethyated product.Product undergoes radical substitution reaction following the Wohl-Ziegler reaction using N-bromosuccinamide and benzoyl peroxide as the radical initiator.In the final step, benzylbromide undergoes SN2 displacement with sodium triazole to give anastrozole.
synthesis of anastrozole

288-88-0 Synthesis

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Yield:120511-73-1 100%

Reaction Conditions:

with potassium tert-butylate in toluene at 9 - 21; for 4.5 h;

Steps:

1.E Example 1 and variations thereof: Preparation of compound of formula II' (anastrozole) by using toluene as the solvent and a phase transfer catalyst

A) Employing toluene in a ratio of approx. 9 : 1 (v/m) relative to compound of formula I' A solution of I' (Z = Br, 328.9 g, 1.0 mol) in toluene (1.32 L) was added to a stirred mixture of K₂CO₃ (179.7 g, 1.3 eq.), 1,2,4-triazole (72.5 g, 1.05 eq.), PEG 600 (30.0 g, 0.05 eq.), and toluene (1.65 L) at 40 - 45 °C. After stirring for 3 h at 44 - 45 °C, the mixture (II' : III' = 8:1, calcd.) was filtered and the residue (III', approx. 41 g, 14 %, purity: 81.2 %), was washed with warm toluene (0.5 L). The filter residue was washed with water and dissolved in warm methanol (500 mL). The resulting solution was evaporated to dryness to give 40.9 g (13.9 %) of isomer III' (81.2 %, HPLC). The filtrate was washed with water, obtaining 3.56 L of a solution of compound II'. HPLC: 89.4 % of compound II', 3.5 % of isomer III' (3.5 %), corresponding to an isomeric ratio of approx. 26:1 (II' : III'). Yield: (91.3 %, calcd.).; E) Employing 2.2 eq of KtOBu [0070] Similar to example 1, item A) but stirring at 9 - 21 °C for 4.5 h. Yield: quantitative. HPLC: 75.16 % of compound II', 3.05 % of isomer III', corresponding to an isomeric ratio of approx. 25:1 (II' : III').

References:

EP2343278,2011,A1 Location in patent:Paragraph 0070

288-88-0 Synthesis

288-88-0
795 suppliers
$10.00/5g