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[ CAS No. 65996-17-0 ]

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Product Details of [ 65996-17-0 ]

CAS No. :65996-17-0 MDL No. :MFCD16610942
Formula : C9H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :244.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 65996-17-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501 UN#:2810
Hazard Statements:H301-H311-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 65996-17-0 ]

* 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 [ 65996-17-0 ]

[ 65996-17-0 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 107-10-8 ]
  • [ 65996-17-0 ]
  • [ 157361-90-5 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 100℃; for 6h;
  • 2
  • [ 10365-98-7 ]
  • [ 65996-17-0 ]
  • [ 119100-84-4 ]
YieldReaction ConditionsOperation in experiment
82% With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating;
  • 3
  • [ 65996-17-0 ]
  • [ 17113-78-9 ]
  • [ 119100-84-4 ]
YieldReaction ConditionsOperation in experiment
94.5% With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 24h; Heating;
  • 4
  • [ 65996-17-0 ]
  • [ 98-80-6 ]
  • [ 58787-21-6 ]
YieldReaction ConditionsOperation in experiment
58% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran for 24h; Heating;
YieldReaction ConditionsOperation in experiment
/BRN= 778458/ (2O), CH3COOH, 30percent HBr-CH3COOH;
  • 6
  • [ 65996-17-0 ]
  • 4-Methyl-2-{propyl-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-nicotinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min 3: 88percent aq. HCOOH / CH2Cl2 / 2 h / Ambient temperature 4: aq. NaOH / ethanol / 1.5 h / Heating
  • 7
  • [ 65996-17-0 ]
  • [ 157361-92-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min 3: 88percent aq. HCOOH / CH2Cl2 / 2 h / Ambient temperature
  • 8
  • [ 65996-17-0 ]
  • 4-Methyl-2-{propyl-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-amino}-nicotinic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 6 h / 100 °C 2: 1.) DMPU, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min
  • 9
  • [ 65996-17-0 ]
  • [ 58787-04-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 58 percent / Pd(PPh3)4, Na2CO3 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid
  • 10
  • [ 65996-17-0 ]
  • [ 105418-67-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid
Multi-step reaction with 2 steps 1: 94.5 percent / Pd(PPh3)4 / tetrahydrofuran / 24 h / Heating 2: 80 percent / polyphosphoric acid
  • 11
  • [ 65996-17-0 ]
  • [ 113583-35-0 ]
  • ethyl 2-bromo-4-[(4,6-dimethoxy-2-pyrimidinyl)methyl]nicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diisopropylamine In tetrahydrofuran; hexane; water; ethyl acetate 27 (Table D, cpd. no. 523) EXAMPLE 27 Preparation of ethyl 2-bromo-4-[(4,6-dimethoxy-2-pyrimidinyl)methyl]nicotinate (Table D, cpd. no. 523) 7.32 g of ethyl 2-bromo-4-methyl nicotinate and 150 ml of THF are cooled in a dry ice/acetone bath under N2 atmosphere, 30 ml of LDA are added over 5 mins and the mixture stirred for 30 mins. 6.55 g of 2-methylsulphonyl-4,6-dimethoxypyrimidine are added as a solid, rinsing with 50 ml of THF, and the mixture stirred cold for 2 hrs and slowly allowed to warm. The THF is evaporated, ca 75 ml of water added and the mixture extracted three times with methylene dichloride. The combined extracts are evaporated and the residue taken up with 20 ml of 25% ethyl acetate/hexane and flash chromatographed using 2 l of 25% ethyl acetate/hexane in 50 ml fractions. Fractions 7 to 14 are combined, evaporated and placed in a Kugelrohr at ca 105° for 2 hrs. The residue is taken up in 20 ml of 10% ethyl acetate/hexane and flash chromatographed with 2 l 10% ethyl acetate/hexane in 50 ml portions to yield title compound (NMR) in fractions 18 to 32.
  • 12
  • [ 65996-17-0 ]
  • [ 164464-52-2 ]
YieldReaction ConditionsOperation in experiment
2.8.4 4. 4. 2-Bromo-4-methyl-3-pyridinecarboxylic Acid 1-Oxide Ethyl Ester Prepared from 2-bromo-4-methyl-3-pyridinecarboxylic acid ethyl ester (for preparation, see Baldwin et al., Journal of Organic Chemistry, 1978, 43, 2529). 1 H NMR (CDCl3): δ 1.39 (3H, t, J=7), 2.29 (3H, s), 4.43 (2H, q, J=7), 7.07 (1H, d, J=7), 8.26 (1H, d, J=7).
  • 13
  • [ 100-67-4 ]
  • [ 65996-17-0 ]
  • [ 952649-80-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide for 14h; Heating;
  • 14
  • [ 3111-52-2 ]
  • [ 65996-17-0 ]
  • [ 952649-85-3 ]
YieldReaction ConditionsOperation in experiment
In ethanol for 14h; Heating;
  • 15
  • [ 65996-17-0 ]
  • [ 62-53-3 ]
  • [ 952649-86-4 ]
YieldReaction ConditionsOperation in experiment
In propionic acid for 6h; Heating;
  • 16
  • [ 65996-17-0 ]
  • [ 100-61-8 ]
  • [ 952649-87-5 ]
YieldReaction ConditionsOperation in experiment
In propionic acid for 6h; Heating;
  • 17
  • [ 105-56-6 ]
  • [ 65996-17-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: piperidine; acetic acid / 24 h / 760.05 Torr / Reflux 2.1: ethanol / 6 h / 760.05 Torr / Reflux 3.1: hydrogen bromide; acetic acid / 2 h / 40 - 55 °C / 760.05 Torr 3.2: 760.05 Torr / Cooling with ice
Multi-step reaction with 3 steps 1: piperidine; acetic acid / 24 h / Reflux 2: ethanol / 6 h / Reflux 3: hydrogen bromide; acetic acid / 2 h / 55 °C
Multi-step reaction with 3 steps 1: acetic acid; piperidine / 18 h / 100 °C 2: toluene; acetic anhydride / 18 h / 50 °C 3: acetic acid; hydrogen bromide / 18 h / 55 °C
Multi-step reaction with 3 steps 1: piperidine; acetic acid / 24 h / 90 °C 2: ethanol / 15 h / 80 °C 3: acetic acid; hydrogen bromide / 15 h / 40 - 55 °C

  • 18
  • [ 759-58-0 ]
  • [ 65996-17-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ethanol / 6 h / 760.05 Torr / Reflux 2.1: hydrogen bromide; acetic acid / 2 h / 40 - 55 °C / 760.05 Torr 2.2: 760.05 Torr / Cooling with ice
Multi-step reaction with 2 steps 1: ethanol / 6 h / Reflux 2: hydrogen bromide; acetic acid / 2 h / 55 °C
Multi-step reaction with 2 steps 1: toluene; acetic anhydride / 18 h / 50 °C 2: acetic acid; hydrogen bromide / 18 h / 55 °C
Multi-step reaction with 2 steps 1: ethanol / 15 h / 80 °C 2: acetic acid; hydrogen bromide / 15 h / 40 - 55 °C

  • 19
  • [ 65996-11-4 ]
  • [ 65996-17-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-carbethoxy-1-cyano-2-methyl-4-dimethylamino-1,4-butadiene With hydrogen bromide; acetic acid at 40 - 55℃; for 2h; Stage #2: With sodium carbonate In water Cooling with ice; ii.D General procedure: Dienoate (D-3) (148 mmol) is dissolved in AcOH (120 mL) and the mixture is stirred at 40 °C.A solution of 45% HBr-AcOH (120 mL) is added dropwise, and then the mixture is stirred at 55 °C for 2 h. The mixture is allowed to cool to RT, poured into ice -water, neutralized with solid Na2C03, and then extracted with ethyl acetate (3 x 150 mL). The combined organic layers are washed with brine (50 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on silica gel (5-20% ethyl acetate-petroether) to afford the product (D-4).
With hydrogen bromide; acetic acid at 55℃; for 2h; 42 Method H; Example 42 Dienoate (H-3) (148 mmol) is dissolved in AcOH (120 mL) and the mixture is stirred at 40 °C. A solution of 45% HBr-AcOH (120 mL) is added dropwise, and then the mixture is stirred at 55 °C for 2 h. The mixture is allowed to cool to RT, poured into ice -water, neutralized with solid Na2C03, and then extracted with ethyl acetate (3 x 150 mL). The combined organic layer is washed with brine (50 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on silica gel (5- 20% ethyl acetate-petroether) to afford the product (H-4).
With hydrogen bromide; acetic acid at 55℃; for 18h; 3 Step 3: Synthesis of Compound WX026-4 10379] WX026-3 (120.00 g, 576.20 mmol, 1.00 eq) was dissolved mAcOH (1.00 E), and H13r/AcOH (1.83 kg, 5.76 mol, 1.00 E, 35% purity, 10.00 eq) was added. The reaction liquid was stirred at 55° C. for 18 h. Afier reaction, the reaction liquid was dried by rotary evaporation, and the crude was purified by chromatographic column (petroleum ether:ethyl acetate=50:1-1:1) to obtain WX026-4. H NMR (400 MHz, CDC13) ö ppm: 8.25 (1H, d, J=5.27 Hz), 7.13 (1H, dd, J=5.02, 0.75 Hz), 4.45 (2H, q, J=7.03 Hz), 2.35 (3H, s), 1.42 (3H, t, J=7.15 Hz).
  • 20
  • [ 65996-17-0 ]
  • [ 1420626-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr 9.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 16 h / 20 °C / 760.05 Torr / Molecular sieve 10.1: tetrahydrofuran / -78 °C / 760.05 Torr / Inert atmosphere 10.2: 760.05 Torr 11.1: triphenylphosphine / tetrahydrofuran / 0.08 h / 0 °C / 760.05 Torr / Inert atmosphere 11.2: 2.33 h / 0 - 20 °C / 760.05 Torr / Inert atmosphere 12.1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr
  • 21
  • [ 65996-17-0 ]
  • [ 1420830-38-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr
  • 22
  • [ 65996-17-0 ]
  • [ 65996-07-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 2-bromo-4-methylnicotinic acid With water; sodium hydroxide In 1,4-dioxane for 12h; Reflux; Stage #2: With hydrogenchloride In water ii.D General procedure: To a solution of 4-substituted ethyl 2-bromolnicotinate (D-4) (52 mmol) in 1,4-dioxane (15 mL), a solution of NaOH (8.0 g, 200 mmol) in H20 (15 mL) is added and the resulting mixture is stirred at reflux for 12 h. The mixture is allowed to cool to RT, diluted with H20, and washed with ethyl acetate (3 x 30 mL). The aqueous layer is acidified with concentrated hydrochloric acid to adjust the pH to 1, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers are washed with brine (25 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo to afford the product nicotinic acid (D-5).
With water; sodium hydroxide In 1,4-dioxane for 12h; Reflux; 42 Method H; Example 42 To a solution of 4 -substituted ethyl 2-bromolnicotinate (H-4) (52 mmol) in 1,4-dioxane (15 mL), a solution of NaOH (8.0 g, 200 mmol) in H20 (15 mL) is added and the resulting mixture is stirred at reflux for 12 h. The mixture is allowed to cool to RT, diluted with H20, and washed with ethyl acetate (3 x 30 mL). The aqueous layer is acidified with concentrated hydrochloric acid to adjust the pH to 1, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers are washed with brine (25 mL), dried over Na2S04 and filtered. The filtrate is concentrated in vacuo to afford the product nicotinic acid (H-5).
  • 23
  • [ 65996-17-0 ]
  • [ 1172130-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr
  • 24
  • [ 65996-17-0 ]
  • [ 1420830-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr
  • 25
  • [ 65996-17-0 ]
  • [ 1420830-36-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere
  • 26
  • [ 65996-17-0 ]
  • [ 1420830-37-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr
  • 27
  • [ 65996-17-0 ]
  • [ 1420830-39-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr
  • 28
  • [ 65996-17-0 ]
  • [ 1420830-40-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr
  • 29
  • [ 65996-17-0 ]
  • [ 1420830-41-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: sodium hydroxide; water / 1,4-dioxane / 12 h / 760.05 Torr / Reflux 1.2: 760.05 Torr / pH 1 2.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 2 h / 20 °C / 760.05 Torr 3.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / 760.05 Torr 4.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 1 h / 90 °C / 760.05 Torr / Inert atmosphere 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / 760.05 Torr 5.2: 2 h / 760.05 Torr 6.1: osmium(VIII) oxide / water; 1,4-dioxane / 0.5 h / 20 °C / 760.05 Torr 6.2: 16 h / 20 °C / 760.05 Torr 7.1: caesium carbonate / ethanol; ethyl acetate / 2 h / 50 °C / 760.05 Torr 8.1: sodium tetrahydroborate; methanol / 16 h / 20 °C / 760.05 Torr 8.2: 760.05 Torr 9.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 16 h / 20 °C / 760.05 Torr / Molecular sieve
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