1H-Indazole-5-carbonitrile,6-fluoro-(9CI) synthesis
- Product Name:1H-Indazole-5-carbonitrile,6-fluoro-(9CI)
- CAS Number:633327-11-4
- Molecular formula:C8H4FN3
- Molecular Weight:161.14
557-21-1
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633335-81-6
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633327-11-4
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105391-70-6
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Yield:-
Reaction Conditions:
Stage #1: zinc(II) cyanide;1-(5-bromo-6-fluoro-1H-indazol-1-yl)ethan-1-one;tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide at 120 - 130; for 36 h;Inert atmosphere;
Stage #2: with water;sodium hydrogencarbonate in ethyl acetate;
Steps:
3; 27; 28
A suspension of 1-acetyl-5-bromo-6-fluoro-1 H-indazoIe (984 mg, 3.83 mmol) (Description 26), zinc cyanide (449 mg, 3.83 mmol), and tetrakis(triphenylphosphine)palladium(0) (442 mg, 0.383 mmol) in DMF (15 mL) was degassed with nitrogen for 15 min then heated at 120°C for 16 h. Additional tetrakis(triphenylphosphine)palladium(0) (442 mg, 0.383 mmol) and DMF (6 mL) were added and the mixture heated at 130°C for a further 20 h. The solution was cooled and ethyl acetate (ca. 60 mL) and saturated aqueous sodium bicarbonate solution (ca. 40 mL) added. The aqueous was separated and further extracted with ethyl acetate (3 x 20 mL) and the organics combined, reduced and purified by chromatography on silica gel eluting with a gradient of 0-80% ethyl acetate in isohexane to afford 6-fluoro-1H-indazole-5-carbonitrile as an off-white solid (246 mg). LCMS (A) m/z: 162 [M+1f, Rt 0.82 min (acidic). In addition, 5-Bromo-6-fluoro-1H- indazole was isolated as a pale yellow solid (384 mg). LCMS (A) m/z: 215/217 [M+1]+, Rt 1.02 min (acidic).
References:
WO2011/72488,2011,A1 Location in patent:Page/Page column 17; 39
557-21-1
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$12.00/5g
105391-70-6
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633327-11-4
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633327-10-3
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633327-11-4
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52723-82-7
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633327-11-4
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633335-81-6
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633327-11-4
45 suppliers
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