129904-48-9|2-Hydroxy-5-(trifluoromethyl)nicotinaldehyde| Ambeed

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Quality Control of [ 129904-48-9 ] Purity: 95% SDS Specification

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Product Details of [ 129904-48-9 ]

CAS No. :	129904-48-9
Formula :	C₇H₄F₃NO₂
M.W :	191.11
SMILES Code :	O=CC1=C(O)N=CC(C(F)(F)F)=C1
MDL No. :	MFCD09909904
InChI Key :	RFGNOPWHPRCTPY-UHFFFAOYSA-N
Pubchem ID :	19819669

Safety of [ 129904-48-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 129904-48-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 129904-48-9 ]

[ 129904-48-9 ] Synthesis Path-Downstream 1~2

1
[ 76041-73-1 ]
[ 68-12-2 ]
[ 129904-48-9 ]

Yield	Reaction Conditions	Operation in experiment
100%		<strong>[76041-73-1]3-Bromo-5-(trifluoromethyl)pyridin-2-ol</strong> (8.20 g, 31.2 mmol) was added in small portions to a suspension of sodium hydride (0.8575 g, 33.94 mmol) in anhydrous THF (76 mL) at room temperature. After complete addition, the reaction mixture was cooled to -78 C. and treated with a 1.7 M solution of tert-butyllithium in pentane (40.0 mL) which was added dropwise via a syringe over a period of 15 min. After stirring for 5 min, anhydrous DMF (8.16 mL, 105 mmol) was added slowly while maintaining the temperature below -50 C. The reaction mixture was then stirred overnight allowing it to warm to room temperature. The resulting light brown mixture was quenched by addition of a saturated NH4Cl solution. The pH of the solution was adjusted to 9-10 by addition of aqueous NaHCO3. The resulting solution was extracted with EtOAc four times. The combined extracts were dried (MgSO4), filtered and concentrated to provide a brown solid crude product (7.33 g, >100% crude yield). MS calculated for C7H4F3NO2 (M+H)+192; found 192.1.
74%	With tert.-butyl lithium; sodium hydride; In tetrahydrofuran; at -78 - 20℃; for 10h;	Under nitrogen, the substituted pyridine described in Step A (48.8g, 202 mmol) was added in small portions to a suspension OF NAH (8. 9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 ML, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N- dimethylformamide (50 ML, 707 mmol) was added slowly to maintain the temperature BELOW-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HC1 and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MGS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).
74%		Step B; Under nitrogen, the substituted pyridine described in Step A, Intermediate 7 (48.8g, 202 mmol) was added in small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N- dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).

74%		Step B; Under nitrogen, the substituted pyridine described in Step A, Intermediate 8 (48.8g, 202 mmol) was added in small portions to a suspension of NaH (8. 9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N, N-dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below-50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HC1 and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgS04, and evaporated i71 vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28. 55 g, 74%).
73.8%		Under nitrogen, the substituted pyridine, described in Step A (48.8 g, 202 mmol) was added by small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous THF (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to -78 C. and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 minutes, DMF (50 mL, 707 mmol) was added slowly to maintain the temperature below -50 C. The resulting mixture was then stirred for 10 hours allowing to warm to room temperature. The mixture was quenched with 2N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexane and filtered to yield a light brown solid (28.55 g, 73.8%). 1H NMR (500 MHz, CD3OD) delta 10.13 (s, 1H), 8.21 (s, 2H).

References: [1]Patent: US2005/267146,2005,A1 .Location in patent: Page/Page column 23.
[2]Patent: WO2004/82682,2004,A1 .Location in patent: Page 48.
[3]Patent: WO2003/93266,2003,A1 .Location in patent: Page/Page column 22.
[4]Patent: WO2005/80371,2005,A1 .Location in patent: Page/Page column 43-44.
[5]Patent: US2007/179158,2007,A1 .Location in patent: Page/Page column 15.

2
[ 76041-73-1 ]
[ 129904-48-9 ]

Yield	Reaction Conditions	Operation in experiment
74%		Under nitrogen, the substituted pyridine described in Step A, Intermediate 11 (48.8 g, 202 mmol) was added in small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous tetrahydrofuran (500 mL). After complete addition of the intermediate, the reaction mixture was cooled to -78 C. and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 min, N,N-dimethylformamide (50 mL, 707 mmol) was added slowly to maintain the temperature below -50 C. The resulting mixture was then stirred for 10 h allowing it to warm to room temperature. The mixture was quenched with 2 N HCl and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexanes and filtered to yield a light brown solid (28.55 g, 74%). 1H NMR (500 MHz, CD3OD) delta 10.13 (s, 1H), 8.21 (s, 2H).
73.8%		Under nitrogen, the substituted pyridine, described in Step A (48.8g, 202 mmol) was added by small portions to a suspension of NaH (8.9 g, 220 mmol) in anhydrous THF (500 ML). After complete addition of the intermediate, the reaction mixture was cooled to-78 C and treated with tert-butyllithium (260 mL, 444 mmol) added dropwise via syringe. After stirring for 5 minutes, DMF (50 mL, 707 mmol) was added slowly to maintain the temperature below- 50 C. The resulting mixture was then stirred for 10 hours allowing to warm to room temperature. The mixture was quenched with 2N HCI and then diluted with ethyl acetate (1000 mL). The organic layer was separated, washed with brine, dried over MGS04, and evaporated in vacuo. The desired product was precipitated out of ethyl acetate and hexane and filtered to yield a light brown solid (28.55 g, 73. 8%). H NMR (500 MHz, CD30D) 8 10.13 (s, 1H), 8.21 (s, 2H).

References: [1]Patent: US2007/117797,2007,A1 .Location in patent: Page/Page column 23.
[2]Patent: WO2004/94371,2004,A2 .Location in patent: Page 59-60.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 129904-48-9 ]

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Trifluoromethyls

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Related Parent Nucleus of
[ 129904-48-9 ]

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CAS No.: 129904-48-9

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