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CAS No. : | 87802-11-7 | MDL No. : | MFCD04972050 |
Formula : | C10H8ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WGAOEHZSJWVLBY-UHFFFAOYSA-N |
M.W : | 209.63 g/mol | Pubchem ID : | 4777711 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.59 |
TPSA : | 42.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.55 cm/s |
Log Po/w (iLOGP) : | 2.24 |
Log Po/w (XLOGP3) : | 2.86 |
Log Po/w (WLOGP) : | 2.61 |
Log Po/w (MLOGP) : | 1.94 |
Log Po/w (SILICOS-IT) : | 2.99 |
Consensus Log Po/w : | 2.53 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.29 |
Solubility : | 0.109 mg/ml ; 0.000519 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.4 |
Solubility : | 0.0829 mg/ml ; 0.000395 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.98 |
Solubility : | 0.0218 mg/ml ; 0.000104 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 5.0h;Cooling with ice; | General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With thionyl chloride; for 2.5h; | To a solution of 5-Chloroindole-2-carboxylic acid (5g,25.6 mmol, 1 eq) in 30 mL of MeOH was added SOCl2 (3.7g,30.8 mmol, 1.2 eq) dropwise within 30 min at 0 C. Subsequently,the reaction mixture was stirred at 35 C for 2 h. Then, the solventwas evaporated under reduced pressure, and the residue was purifiedby column chromatography using ethylacetate/petroleum,giving intermediate 2 as a yellow solid, yield 93%. m.p.212.2-214.7 C. 1H NMR (400 MHz, CDCl3) delta 8.95 (s, 1H, NH), 7.67 (s,1H, ArH), 7.35 (d, J 8.7 Hz, 1H, ArH), 7.31-7.25 (m, 2H, ArH, ArCH), 3.95 (s, 3H, OCH3); 13C NMR (100 MHz, CDCl3) delta 162.1, 135.1, 128.4,126.6, 126.0, 121.8, 112.98, 112.93, 108.1, 52.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 5-chloroindole-2-carboxylate With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: 3-(bromomethyl)-5-(5-chlorothiophen-2-yl)isoxazole In N,N-dimethyl-formamide at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With boron trifluoride diethyl etherate In dichloromethane at 20 - 45℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With aluminium trichloride In dichloromethane at 20℃; for 24h; | |
33% | With iodine In neat (no solvent) at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 13h; | 1 Preparation of methyl 5-chloro-1-methyl-1H-indole-2-carboxylate 89 mg (0.42 mmol) of methyl 5-chloro-lH-indole-2-carboxylateAnd 174 mg (1.26 mmol) of potassium carbonate were dissolved in 2 ml of DMF, and 31 ul (0.50 mmol) of iodomethane was added,Add At 50 ° CStir for 13 hours.After completion of the reaction, the reaction mixture was extracted with 125 ml of ethyl acetate, washed with saturated sodium chloride and water, and dried over anhydrous sodium sulfate.The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (normal hexane: ethyl acetate = 10: 1, v / v) to obtain 81 mg (0.36 mmol) of the title compound as a white solid in 86% yield. |
With potassium hydroxide In acetone at 0 - 20℃; | ||
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 84% 2: 13% | In toluene at 60℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 81 percent / sodium methoxide / methanol / 4 h / -10 °C 2: 84 percent / Rh2(pbf)4 / toluene / 16 h / 60 °C | ||
Multi-step reaction with 2 steps 1: sodium; methanol / -10 °C 2: 5,5-dimethyl-1,3-cyclohexadiene / 2 h / 140 °C | ||
Multi-step reaction with 2 steps 1: sodium / methanol; dichloromethane / -78 - 20 °C 2: o-xylene / 0.83 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C 4.1: 33 percent / Grubbs' catalyst Ru627 / CH2Cl2 / 39 h / Heating 5.1: 3,5-dinitrobenzoic acid; (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one / toluene / 36 h / -40 °C 5.2: NaBH4 / methanol / 0.25 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C 4.1: 33 percent / Grubbs' catalyst Ru627 / CH2Cl2 / 39 h / Heating 5.1: 3,5-dinitrobenzoic acid; (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one / toluene / 36 h / -40 °C 5.2: NaBH4 / methanol / 0.25 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: KOH / acetone / 0 - 20 °C 2: LiAlH4 / tetrahydrofuran / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C 4.1: 33 percent / Grubbs' catalyst Ru627 / CH2Cl2 / 39 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C 4.1: 33 percent / Grubbs' catalyst Ru627 / CH2Cl2 / 39 h / Heating 5.1: 3,5-dinitrobenzoic acid; (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one / toluene / 36 h / -40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: KOH / acetone / 0 - 20 °C 2.1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3.1: NaH / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: tetrahydrofuran / 2 h / 20 °C 4.1: 33 percent / Grubbs' catalyst Ru627 / CH2Cl2 / 39 h / Heating 5.1: 3,5-dinitrobenzoic acid; (2S,5S)-5-benzyl-2-tert-butyl-3-methyl-imidazolidin-4-one / toluene / 36 h / -40 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 20 °C 1.2: dimethylformamide / 80 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 20 °C 1.2: dimethylformamide / 80 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran / 60 °C 3.1: NEt3; bis(oxo-3-oxazolidinyl)phosphoryl chloride / CH2Cl2 / 20 °C 3.2: CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / BF3*Et2O / CH2Cl2 / 4 h / 20 - 45 °C 2: 58 percent / MCPBA / CHCl3 / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / BF3*Et2O / CH2Cl2 / 4 h / 20 - 45 °C 2: 58 percent / MCPBA / CHCl3 / 1.5 h / 20 °C 3: 89 percent / aq. NH3; NH4Cl / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: 74 percent / n-Bu3P / tetrahydrofuran / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: 74 percent / n-Bu3P / tetrahydrofuran / 3 h / 20 °C 3: 55 percent / NaH / dimethylformamide / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: 74 percent / n-Bu3P / tetrahydrofuran / 3 h / 20 °C 3: 55 percent / NaH / dimethylformamide / 6 h / 20 °C 4: 46 percent / monoperoxyphthalic acid magnesium salt (MMPP) / methanol / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid In methanol | 36 Preparation of Methyl 5-chloroindole-2-carboxylate Preparation of Methyl 5-chloroindole-2-carboxylate 5-Chloroindole-2-carboxylic acid (0.95 g, 4.65 mmol) was dissolved in methanol (35 ml) and treated with sulphuric acid (0.5 ml). The mixture was refluxed for 5 h and cooled and the solvent was removed. The residue was recrystallized twice from methanol to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; ethyl acetate | 36 Preparation of Methyl 5-chloroindoline-2(R/S)-carboxylate Preparation of Methyl 5-chloroindoline-2(R/S)-carboxylate Methyl 5-chloroindole-2-carboxylate (0.6 g, 2.87 mmol) and magnesium shavings (0.34 g, 14.3 mmol) were suspended in methanol (40 ml) and the mixture was stirred for 8 h. The mixture was filtered, treated with methylene chloride (100 ml) and washed with NH4Cl solution. The organic fraction was dried (Na2SO4) and the solvent removed in order to give a solid which was purified by chromatography on a column of silica gel, using a 7/3 petroleum/ethyl acetate mixture as eluent. The product was isolated in the form of a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; sodium In methanol | D Methyl-5-chloroindole-2-carboxylate Method D Methyl-5-chloroindole-2-carboxylate Sodium (10.3 g, 447 mmol) was dissolved in methanol (HPLC grade, anhydrous, 150 ml) with continual stirring under an atmosphere of argon. Upon complete dissolution of the sodium ethyl-5-chloroindole-2-carboxylate (10.08 g, 44.7 mmol) was added as a single portion and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was acidified with the addition of aqueous hydrochloric acid (excess) causing the precipitation of a white solid. The solid was filtered and washed with aqueous hydrochloric acid (100 ml) and water (100 mls) then dried overnight in at 55° to yield the product as a white solid (8.97 g, 95%). NMR δ (CD3SOCD3) 3.86 (s, 3H), 7.12 (dd, 1H), 7.24 (dd, 1H), 7.43 (d, 1H), 7.72 (s, 1H), 12.10 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine In tetrahydrofuran at 110℃; for 20h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With caesium carbonate; cesium fluoride In 1,2-dimethoxyethane at 90℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With aluminum (III) chloride In 1,2-dichloro-ethane at 25 - 110℃; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 5,10,15,20-tetrakis(pentafluorophenyl)-21H,23H-porphyrin iron(III) chloride In 1,2-dichloro-ethane for 24h; Molecular sieve; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrazine hydrate In ethanol for 5h; Reflux; | |
With hydrazine hydrate | ||
With hydrazine hydrate In methanol for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(I) oxide; caesium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 16h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; water for 2.5h; Reflux; Inert atmosphere; Acidic conditions; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Cooling with ice; | 9-1.1 Step 1: Preparation of methyl 5-chloro- 1-(phenylsulfonyl)- 1H-indole-2-carboxylate To a suspension of methyl 5-chloro-1H-indole-2-carboxylate (7.56 g, 36.0 mmol, CAS No.: 105 17-21-2) and sodium hydride (1.70 g, 43.0 mmol, 60% purity in mineral oil) in N,Ndimethylfonnamide (100 mL) was added benzenesulfonyl chloride (6.1 mL, 47.0 mmol, CAS No.: 98-09-9) dropwise in an ice-water bath. After being stirred at room temperature for 2 hours, the mixture was then poured into ice-water (100 mL). The resulting precipitate was collected by filtration, which was washed with petroleum ether (50 mL), and then dried in vacuo to afford11.6 g of methyl 5-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate as a pale white solid (yield was 92%). |
92% | With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; Cooling with ice; | 18.1 Step 1: Preparation of methyl 5-chloro- 1-(phenylsulfonyl)- 1H-indole-2-carboxylate To a suspension of methyl 5-chloro-1H-indole-2-carboxylate (7.56 g, 36.0 mmol, CAS No.: 105 17-21-2) and sodium hydride (1.70 g, 43.0 mmol, 60% purity in mineral oil) in N,Ndimethylformamide (100 mL) was added benzenesulfonyl chloride (6.1 mL, 47.0 mmol) dropwise in an ice-water bath. After being stirred at room temperature for 2 hours, the mixture was then poured into ice water (100 mL). The precipitate was collected by filtration, which was washed with petroleum ether (50 mL), and then dried in vacuo to afford 11.6 g of methyl 5- chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate as a pale white solid (yield was 92%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; [bis(acetoxy)iodo]benzene In toluene at 110℃; for 3h; Inert atmosphere; Schlenk technique; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With N-chloro-N-methoxybenzenesulfonamide In acetonitrile at 20℃; for 5h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With aluminum (III) chloride In 1,2-dichloro-ethane at 110℃; for 0.0333333h; Microwave irradiation; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With aluminum (III) chloride In 1,2-dichloro-ethane at 110℃; for 0.0333333h; Microwave irradiation; Sealed tube; | |
21% | With aluminum (III) chloride In 1,2-dichloro-ethane at 25 - 100℃; for 0.05h; Microwave irradiation; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With dipotassium peroxodisulfate; sodium nitrite In N,N-dimethyl-formamide at 80℃; for 2h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 5-chloroindole-2-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 1-Chloro-4-(chloromethyl)benzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; | 4.1.2. 1-Benzyl-5-chloro-1H-indole-2-carboxylic acid (3a-b) General procedure: To a stirred suspension of NaH (60% dispersion inmineral oil;0.7 g, 17.3 mmol, 1.2 eq) in DMF (10 mL) was added dropwise solutionof 1 (3g, 14.4 mmol, 1 eq) in DMF (30 mL) at 0 °C, and themixturewas stirred at room temperature for 30 min. To the mixturewas added dropwise 4-Chlorobenzyl chloride or 4-Fluorobenzylchloride (14.4 mmol, 1 eq), and the resulting mixturewas stirredat room temperature for 30 min. The reaction was quenched withwater and acidified with acetic acid. The formed precipitate wasfiltered, washed with water, and dried under vacuum to obtain thegray solid.To a solution of the above compounds (7.8 mmol, 1 eq) inethanol (30 mL), 10% NaOH solution (15 mL) was added with stirringfor 15 min at 75 °C. The residue after removal of ethanol underreduced pressure was then taken into water and acidified withconcentrated hydrochloric acid. The formed precipitate wasfiltered, washed with water, and dried under vacuum to give 3a-bas white solid. 4.1.2.1. 5-chloro-1-(4-chlorobenzyl)-1H-indole-2-carboxylic acid(3a). Compound 3a was synthesized according to the syntheticprocedure given above as white solid in yield of 85%, 1H NMR(400 MHz, DMSO-d6) δ 7.80 (d, J= 2.0 Hz, 1H, ArH), 7.61 (d,J= 8.9 Hz, 1H, ArH), 7.37e7.29 (m, 4H, ArH, ArCH=), 7.05-7.01 (m,2H, ArH), 5.87 (s, 2H, NCH2Ar), COOH (none); ESI-Mass forC16H11Cl2NO2: m/z (M+ H)+ 317.7. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: methyl 5-chloroindole-2-carboxylate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: 1-chloromethyl-4-fluorobenzene In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; | 4.1.2. 1-Benzyl-5-chloro-1H-indole-2-carboxylic acid (3a-b) General procedure: To a stirred suspension of NaH (60% dispersion inmineral oil;0.7 g, 17.3 mmol, 1.2 eq) in DMF (10 mL) was added dropwise solutionof 1 (3g, 14.4 mmol, 1 eq) in DMF (30 mL) at 0 °C, and themixturewas stirred at room temperature for 30 min. To the mixturewas added dropwise 4-Chlorobenzyl chloride or 4-Fluorobenzylchloride (14.4 mmol, 1 eq), and the resulting mixturewas stirredat room temperature for 30 min. The reaction was quenched withwater and acidified with acetic acid. The formed precipitate wasfiltered, washed with water, and dried under vacuum to obtain thegray solid.To a solution of the above compounds (7.8 mmol, 1 eq) inethanol (30 mL), 10% NaOH solution (15 mL) was added with stirringfor 15 min at 75 °C. The residue after removal of ethanol underreduced pressure was then taken into water and acidified withconcentrated hydrochloric acid. The formed precipitate wasfiltered, washed with water, and dried under vacuum to give 3a-bas white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 60 °C 2.1: sodium hydroxide; water / methanol / 1 h / 65 °C 3.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 0.08 h / 20 °C 3.2: 1.5 h / 20 °C 4.1: sodium hydroxide; water / methanol / 1 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With potassium carbonate In N,N-dimethyl-formamide at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4h; Inert atmosphere; |
Tags: 87802-11-7 synthesis path| 87802-11-7 SDS| 87802-11-7 COA| 87802-11-7 purity| 87802-11-7 application| 87802-11-7 NMR| 87802-11-7 COA| 87802-11-7 structure
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Precautionary Statements-General | |
Code | Phrase |
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Code | Phrase |
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P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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