1H-Indazole,6-fluoro-3-methyl-(9CI) synthesis
- Product Name:1H-Indazole,6-fluoro-3-methyl-(9CI)
- CAS Number:159305-16-5
- Molecular formula:C8H7FN2
- Molecular Weight:150.15
364-83-0
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159305-16-5
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Yield:159305-16-5 83.2%
Reaction Conditions:
with hydrazine hydrate in N,N-dimethyl-formamide at 120; for 14 h;
Steps:
73.1 Step-i: Synthesis of 6-fluoro-3-methyl-iH-indazole
To a solution of 4-bromo-2-fluoro-5-nitrobenzaldehyde (23 g, 93.11 mmol) in DMF (350mL) was added hydrazine (6 mL, 102 mmol) and the contents were heated at 150 °C for 2 h.After completion of reaction, reaction mixture was cooled to room temperature, diluted with ethyl acetate. The organic layer was washed with water, brine solution and dried over anhydrous Na2SO4, concentrated under reduced pressure to obtain the title compound (20.0 g, 93%) as a yellow solid.‘H NMR (400 MHz, DMSO-d6): ? 13.70 (bs, 1H), 8.63 (s, 1H), 8.36 (s, 1H), 8.06 (s, 1H).LCMS: mlz: 240 (M-1) .Using the similar reagents and conditions as described in step 2 of example 5, 1-(2,4- difluorophenyl)ethan-1-one (2gm, 12.8098mmo1) was cyclized using hydrazine hydrate (1.28gm, 25.6196mmo1) in DMF (lOmL) at 120°C for 14h to obtain the crude product. This was purifiedby silica gel column chromatography and with 30%ethyl acetate in hexane to get the titled product (1.6gm, 83.20%). LCMS: mlz = 151.2 (M+1).
References:
WO2015/104662,2015,A1 Location in patent:Page/Page column 44; 110
1979-36-8
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159305-16-5
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159305-15-4
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159305-16-5
53 suppliers
$200.00/100mg