4-(3-Acetyl-8-bromo-3H-pyrazolo[3,4-c]quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile synthesis

11synthesis methods

Product Name:4-(3-Acetyl-8-bromo-3H-pyrazolo[3,4-c]quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile
CAS Number:1201643-72-2
Molecular formula:C22H17BrN4O
Molecular Weight:433.3

Benzeneacetonitrile, 4-[(3-amino-6-bromo-4-quinolinyl)methyl]-α,α-dimethyl-

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4-(3-Acetyl-8-bromo-3H-pyrazolo[3,4-c]quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile

1201643-72-2
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Yield:1201643-72-2 52%

Reaction Conditions:

with potassium acetate in toluene;

Steps:

1.II.1

To a solution of compound 10 (380 mg, 1 mmol) in toluene (50 mL) was added KOAc (200 mg, 2 mmol) and acetic anhydride (300 mg). The reaction was monitored by HPLC for the consumption of starting material. To the reaction mixture was charged isoamylnitrite (120 mg, 1.2 mmol). The resulting mixture was heated to 8O⁰C and stirred for 18 h, at which time HPLC of an aliquot indicated the reaction was complete. The solution was concentrated and the residue was purified by column (EA:PE = 1 : 10 to 1:5) to give compound 11 (250 mg, 52%) as a light yellow solid. MS (m/z) (M⁺+H): 432, 434; ¹H-NMR (δ, 400MHz, DMSO-d6, ppm), 9.92 (s, IH), 8.18 (d, IH, J=8.8Hz), 8.12 (d, IH, J=2.20Hz), 7.84-7.95 (m, 4H), 2.84 (s, 3H, Ac), 1.82 (s, 6H, 2CH₃).

References:

WO2009/155527,2009,A2 Location in patent:Page/Page column 142-143

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