Home Cart 0 Sign in  

[ CAS No. 186446-26-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 186446-26-4
Chemical Structure| 186446-26-4
Structure of 186446-26-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 186446-26-4 ]

Related Doc. of [ 186446-26-4 ]

Alternatived Products of [ 186446-26-4 ]

Product Details of [ 186446-26-4 ]

CAS No. :186446-26-4 MDL No. :MFCD09835295
Formula : C9H5ClFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 213.59 Pubchem ID :-
Synonyms :

Safety of [ 186446-26-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 186446-26-4 ]

* 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 [ 186446-26-4 ]

[ 186446-26-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 127-17-3 ]
  • [ 186446-26-4 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 4-chloro-3-fluoro-2-iodoaniline With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 15℃; for 0.5h; Stage #2: 2-oxo-propionic acid In N,N-dimethyl-formamide at 36℃; for 0.333333h; Stage #3: In N,N-dimethyl-formamide at 100℃; for 3h; 7 Compound 105[00329] Compound 104 (74.5g, 0.275mol) was added to a 2L four-neck round bottom flask equipped with overhead stirrer, reflux condenser, heating mantle, temperature controller, 250ml addition funnel, an internal temperature probe and an argon inlet. N,N- Dimethylformamide (575ml) was charged to the flask at room temperature. DABCO (95.5g, 0.85 lmol) was added in one portion and the internal temperature dropped to 150C. The mixture was stirred for 20min to effect dissolution and the solution was degassed by bubbling argon through it vigorously for lOmin. Pyruvic acid (57.33ml, 0.824mol) was added to the brown solution over lOmin and the internal temperature rose to 360C. The solution was again degassed with argon for lOmin and palladium acetate (678mg, 0.0030mol) was added in one portion.[00330] The mixture was heated to 1000C for 3h after which time analysis by HPLC method Test 20 (MeCN, filtered) indicated complete conversion of starting material (Rt 5.44min) to one product (Rt 3.64min). The reaction was cooled to room temperature for 15h and subsequently to 50C. A solution of hydrochloric acid (1.15N, 575ml then 0.1 15N, 280ml) was added gradually keeping the temperature below 1O0C, monitoring the "pH" until pH = 3.5. A tan solid precipitated from the solution and the mixture was stirred for an additional 0.5h at 50C. The solid was filtered under vacuum and washed with 1O0C water (3 x 200ml). After drying at 4O0C under vacuum for 36h, Compound 105 (55.9g, 95% yield) was obtained. Compound 105: C9H5ClFNO2 213.59gmol'' HPLC analysis (Test 20, MeCN): Rt 3.63min; 99% purity (at) 272nm ESI -ve: m/z 212.1 [M-H]" 10%; 168.1 [M- COOH]" 100% 1H NMR δH (400 MHz, d6-DMSO): 7.10, 7.11 (IH, d, Ar-H), 7.25-7.32 (2H, m, 2 x Ar-H), 12.30, 13.33 (2 x 1Η, 2 x s, N-H, COO-H) '3C NMR δc (100 MHz, d6- DMSO): 102.45 (C-3), 108.76, 108.92 (C-9), 110.20, 110.24 (C-6), 116.88, 117.09 (C-5), 125.46 (C-7), 130.34 (C-2), 137.90, 138.00 (C-8), 149.76, 152.25 (C-4), 162.12 (C=O) 19F NMR δF (376 MHz, d6-DMSO): -121.35 (IF, d).
  • 2
  • [ 480450-89-3 ]
  • [ 186446-26-4 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: methyl 5-chloro-4-fluoro-1H-indole-2-carboxylate With water; lithium hydroxide In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran; water
Stage #1: methyl 5-chloro-4-fluoro-1H-indole-2-carboxylate With lithium hydroxide; water In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In water 274 The compound obtained in Referential Example 273 (440 mg) was dissolved in tetrahydrofuran (10 mL), and an aqueous solution (5 mL) of lithium hydroxide (160 mg) was added thereto, followed by stirring at room temperature for 3 hours. To the reaction mixture was further added an aqueous solution (5 mL) of lithium hydroxide (240 mg), and the thus-obtained mixture was stirred at room temperature for an additional 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was neutralized with 1N aqueous HCl. The thus-obtained mixture was extracted with ethyl acetate 3 times, and the organic layers were combined. The combined organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, to thereby give the title compound (390 mg).1H-NMR(DMSO-d6) δ:6.79(1H, s), 7.16-7.26(2H, m) MS(FAB)m/z:214(M+H)+.
With lithium hydroxide; sodium chloride In tetrahydrofuran R.274 5-Chloro-4-fluoroindole-2-carboxylic acid: REFERENTIAL EXAMPLE 274 5-Chloro-4-fluoroindole-2-carboxylic acid: The compound (440 mg) obtained in Referential Example 273 was dissolved in tetrahydrofuran (10 ml), an aqueous solution (5 ml) of lithium hydroxide (160 mg) was added, and the mixture was stirred at room temperature for 3 hours. After an aqueous solution (5 ml) of lithium hydroxide (240 mg) was additionally added to the reaction mixture, and the mixture was stirred for additional 1 hour, the reaction mixture was concentrated under reduced pressure. The residue was neutralized with 1N hydrochloric acid and extracted 3 times with ethyl acetate. The resultant organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (390 mg). 1H-NMR (DMSO-d6) δ: 6.79(1H,s), 7.16-7.26(2H,m). MS (FAB) m/z: 214(M+H)+.
With lithium hydroxide In tetrahydrofuran; water 274 5-Chloro-4-fluoroindole-2-carboxylic acid: [Referential Example 274] 5-Chloro-4-fluoroindole-2-carboxylic acid: The compound (440 mg) obtained in Referential Example 273 was dissolved in tetrahydrofuran (10 ml), an aqueous solution (5 ml) of lithium hydroxide (160 mg) was added, and the mixture was stirred at room temperature for 3 hours.. After an aqueous solution (5 ml) of lithium hydroxide (240 mg) was additionally added to the reaction mixture, and the mixture was stirred for additional 1 hour, the reaction mixture was concentrated under reduced pressure.. The residue was neutralized with 1N hydrochloric acid and extracted 3 times with ethyl acetate.. The resultant organic layers were combined, washed with saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate.. The solvent was distilled off under reduced pressure to obtain the title compound (390 mg).1H-NMR (DMSO-d6) δ: 6.79(1H,s), 7.16-7.26(2H,m). MS (FAB) m/z: 214(M+H)+.

  • 3
  • [ 186446-26-4 ]
  • [ 186446-27-5 ]
  • S-6-chloro-4-fluoro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
115 S-5-Chloro4-fluoro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide and S-6-chloro-4-fluoro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide EXAMPLE 115 S-5-Chloro4-fluoro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide and S-6-chloro-4-fluoro-1H-indole-2-carboxylic acid (1-benzyl-2-oxo-2-thiazolidin-3-yl-ethyl)-amide From a mixture of 5-chloro-4-fluoro-1H-indole-2-carboxylic acid and 6-chloro-4-fluoro-1H-indole-2-carboxylic acid, and S-2-amino-3-phenyl-1-thiazolidin-3-yl-propan-1-one. mp 105-125° C. dec. Anal. Calcd.: C, 58.40; H, 4.43; N, 9.73; Found: C, 58.54; H, 4.59; N, 9.58.
  • 4
  • [ 67-56-1 ]
  • [ 186446-26-4 ]
  • [ 480450-89-3 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 5-chloro-4-fluoro-1H-indole-2-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20 - 25℃; for 3h; Inert atmosphere; Stage #2: methanol In N,N-dimethyl-formamide at 20 - 25℃; for 3h; Inert atmosphere;
  • 6
  • [ 1018450-37-7 ]
  • [ 127-17-3 ]
  • [ 186446-26-4 ]
YieldReaction ConditionsOperation in experiment
1 g With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; In N,N-dimethyl-formamide; at 100℃; for 3h;Inert atmosphere; To a solution of 1008 (3.0 g, 11.07 rnmoi) in DMF (40 ml) was added pyruvic acid (2.4 mL, 33.2 mrnol) and DABCO (3.7 mL, 33.2 nunol). Then the reaction mixture was degassed with argon for 10 miii and Pd(OAc)2 (246 mg) was added. After stirring the reaction mixture at 100C for 3 h, water (15 ml) was added to the reaction mixture and then extracted with EtOAc (2 x 30 mL). The combined organic layers were dried over anhydrous Na2SO4 andconcentrated under reduced pressure, The crude residue was purified h Comhit?Iash column chromatography (hexane/EtOAc, 1:2) to afford 1009 (1.0 g, 43%) as a solid. ?H NMR (300 MHz, DMSO-c4?): d 12.32 (s, IH), 7.31 (q, 2H), 7.12 (s, IH).
  • 7
  • [ 4318-37-0 ]
  • [ 186446-26-4 ]
  • [ 1394078-66-0 ]
YieldReaction ConditionsOperation in experiment
General procedure: (5-Chloro-7-fluoro-1H-indole-2-yl)-carboxylic acid (5a) (50 mg, 0.23 mmol), N,N-diisopropylethylamine (82 mul, 0.47 mmol) and 2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (89 mg, 0.23 mmol) were dissolved in 550 mul N,N-dimethylformamide. After stirring for 10 min 4-methyl-piperazin 6a (26 mul, 0.23 mmol) was added and the reaction mixture was stirred for 16 h at 20 C. The solvent was evaporated under reduced pressure and the crude product was purified using chromatography method P1, yielding 37 mg (53%) of the title compound.
Same Skeleton Products
Historical Records