1-(6-(trifluoroMethyl)pyridin-3-yl)ethanone synthesis
- Product Name:1-(6-(trifluoroMethyl)pyridin-3-yl)ethanone
- CAS Number:358780-14-0
- Molecular formula:C8H6F3NO
- Molecular Weight:189.13
358780-13-9
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108-59-8
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358780-14-0
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Yield:358780-14-0 79%
Reaction Conditions:
Stage #1:malonic acid dimethyl ester with triethylamine;magnesium chloride in toluene for 2.5 h;light cooling;
Stage #2:6-(trifluoromethyl)nicotinoyl chloride in toluene for 2 h;Cooling;
Stage #3: with hydrogenchloride;watermore than 3 stages;
Steps:
6.i
i) l-(6-Trifluoromethyl-pyridin-3-yl)-ethanone. Magnesium chloride 3.18 g (33.4 mmol) was suspended in 160 ml toluene. After the addition of triethylamine 16.63 ml (119.3 mmol) and malonic acid dimethyl ester 6.58 ml (57.3 mmol) the reaction mixture was stirred for 2.5 hours under light cooling. 6-Trifluoromethyl-nicotinoyl chloride was dissolved in 15 ml toluene and added dropwise under cooling to the reaction mixture. After stirring for 2 hours the mixture was acidified with cone, hydrochloric acid (15 ml). A white precipitate was formed which was dissolved by the addition of water. The water was separated and extracted one time with ethyl acetate and one time with dichloromethane. The combined organic layers were evaporated and the residue was dissolved in 52 ml dimethyl sulfoxide (DMSO) and 2 ml water. The obtained solution was stirred at155 0C for 2.5 hours. After cooling and the addition of 100 ml ice water it was stirred for 15 minutes. The product was isolated by suction and washed with ice water (3 x 15 ml). The solid was dried at 400C to give 7.11 g (79%) of the title compound as white solid. MS: 189.90 (ESI+)1H-NMR (400 MHz, [D6]DMSO): δ = 2.69 (s, 3H, CH3), 8.08 (d, IH, 5-H-pyridine), 8.56 (d, IH, 4-H-pyridine), 9.26 (s, IH, 2-H-pyridine)
References:
F. HOFFMANN-LA ROCHE AG WO2008/34579, 2008, A1 Location in patent:Page/Page column 24-25
416852-53-4
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75-16-1
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358780-14-0
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$32.00/100mg
97674-02-7
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436799-32-5
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358780-14-0
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$32.00/100mg
917-64-6
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416852-53-4
11 suppliers
$450.00/1 g
358780-14-0
120 suppliers
$32.00/100mg
75-16-1
265 suppliers
$12.00/10ml
216431-85-5
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$8.00/1g
358780-14-0
120 suppliers
$32.00/100mg