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CAS No. : | 39416-48-3 | MDL No. : | MFCD00013223 |
Formula : | C5H6Br3N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 319.82 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 0.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.91 |
TPSA : | 14.14 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.45 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.94 |
Log Po/w (WLOGP) : | -0.8 |
Log Po/w (MLOGP) : | 1.95 |
Log Po/w (SILICOS-IT) : | 1.85 |
Consensus Log Po/w : | 1.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.8 |
Solubility : | 0.00509 mg/ml ; 0.0000159 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.94 |
Solubility : | 0.037 mg/ml ; 0.000116 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.91 |
Solubility : | 3.95 mg/ml ; 0.0124 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.34 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P264-P270-P271-P280-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 | UN#: | 3261 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* 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 |
---|---|---|
With sodium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; chloroform; 4-Methylphenethyl alcohol; | EXAMPLE 7 [3-(2-Acetylamino-ethyl)-2-phenyl-1H-indol-5-yl]-carbamic acid methyl ester 2-[2-(5-Nitro-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione (1 mmol) is dissolved in THF/chloroform (1:1) and treated with <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> at 0 C. for 90 min, then eluted from a silica column with chloroform-methanol. The product is dissolved in toluene-ethanol (1:1) and treated with phenylboronic acid (1.5 equiv), sodium carbonate (2.5 equiv), lithium chloride (3 equiv), and palladium tetrakis(triphenylphosphine) (5 mol %). The mixture is refluxed 4 h, concentrated in vacuo, and the oil chromatographed on silica eluted with ethyl acetate-hexane to afford 2-[2-(5-nitro-2-phenyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.12 g (98%) | With acetic acid; zinc; In tert-butyl alcohol; | PBPB (2.8 g, 7.8 mmol) was added portionwise to the (3-chloro-4-fluoro-phenyl)-(7-methyl-7H-pyrrolo [2,3-d]pyrimidin-4-yl)-amine (1.08 g, 3.9 mmol) suspended in tert-butanol (20 mL) and acetic acid (10 mL). After stirring at room temperature for 18 hours, to the mixture was added zinc dust (760 mg, 11.7 mmol) portionwise and stirring was continued for overnight. The precipitate was filtered off and the filtrate was concentrated. The residue was triturated with little water and the precipitate was collected by vacuum filtration, washed with little ethyl acetate and dried to give 1.12 g (98%) of 4-(3-chloro-4-fluoro-phenylamino)-7-methyl-5,7-dihydro-pyrrolo [2,3-d]pyrimidin-6-one as a tan colored solid. 1H NMR (DMSO-d6) 9.07 (s, 1H, NH), 8.42 (s, 1H), 8.01 (d, J=2.6 & 7.2Hz, 1H), 7.56 (m, 1H), 7.34 (t, J=9.1 Hz, 1H), 3.48 (s, 2H, CH2), 3.07 (s, 3H, CH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; magnesium sulfate; trifluoroacetic acid; In dichloromethane; | Example 12 (R)-5-bromo-6-ethoxy-2,3-dihydro-N,N-dipropyl-1H-inden-2-amine Hydrochloride (X) Pyridinium perbromide (64 kg, 1.34 equiv.) is added to dichloromethane solvent and cooled to -20. A -20 solution of (S)-5-ethoxy-2,3-dihydro-N,N-dipropyl-1H-inden-2-amine (IX, EXAMPLE 9, 39 kg) and trifluoroacetic acid (50 kg, 3.0 equiv) dissolved in dichloromethane is added. After stirring for several hours the reaction is warmed to 0. When analysis indicated that all of the starting material (IX) had been consumed, the reaction is quenched with a reducing agent such as aqueous sodium bisulfate. Aqueous sodium hydroxide is then added to make the pH greater than 12 and most of the dichloromethane and pyridine are removed by heating under reduced pressure. The residue is extracted several times with methyl t-butyl ether, the organic layers are combined, stirred with magnesium sulfate, filtered, and the solvent removed by heating under reduced pressure to give the title compound in crude form. An analytical sample is crystallized from methanol/methyl t-butyl ether as the hydrochloride salt to give the title compound as the hydrochloride salt in purified form, mp=202-204. The free base of the title compound has the following characteristics, NMR (300 MHz, CDCl3) delta 0.86, 1.41-1.55, 2.43-2.49, 2.76-2.99, 3.57, 4.05, 6.73, 7.31; [alpha]25D=5 (c=1.01, methanol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tert-butyl alcohol; | a 3,3-Dibromo-7-azaoxindole A solution of 7-azaindole (4.0 g, 34 mmol) in tert-BuOH (200 mL) is stirred at room temperature and <strong>[39416-48-3]pyridinium perbromide</strong> (32.5 g, 0.1 mol) is added in portions over 30 min. and the reaction mixture is stirred for 3 hours. Pyridinium perbromide (10.8 g, 33 mmol) is added and the mixture is stirred for a further 2 hours. The tert-BuOH is evaporated under educed pressure and the residue is partitioned between water (300 mL) and EtOAc (300 mL). The organic layer is separated and the aqueous layer is extracted with EtOAc. The combined organic layers are washed with water (2*50 mL), and brine. The organic layer is dried over anhydrous MgSO4, filtered and the solvent evaporated. Trituration of the residue with CH2Cl2 gives a white solid which is collected by filtration and dried under vacuum to give 3,3-dibromo-7-azaoxindole, 8.35 g. 1H-NMR (DMSO-d6) delta11.99 (s, 1H), 8.21 (dd, 1H, J=5.1, 1.5 Hz), 8.00 (dd, 1H, J=7.5, 1.5 Hz), 7.17 (dd, 1H, J=7.5, 5.1 Hz). MS (+ve ES) 293 (28), (M+H), 147 (100). | |
In tert-butyl alcohol; | a 3,3-dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of pyrrolo[2,3-b]pyridine (4.0 g, 34 mmol) in tert-BuOH (200 mL) was stirred at room temperature and <strong>[39416-48-3]pyridinium perbromide</strong> (32.5 g, 0.1 mol) was added in portions over 30 min, and the reaction mixture was stirred for 3 hours. Pyridinium perbromide (10.8 g, 33 mmol) was added, and the mixture was stirred for a further 2 hours. The tert-BuOH was evaporated under reduced pressure, and the residue was partitioned between water (300 mL) and EtOAc (300 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (2*50 mL) and brine. The organic layer was dried over anhydrous MgSO4 and filtered, and the solvent was evaporated. Trituration of the residue with CH2Cl2 gave a white solid which was collected by filtration and dried under vacuum to provide 8.35 g of the title compound. 1H NMR (d6-DMSO) delta11.99 (s, 1H), 8.21 (dd, 1H, J=5.1 Hz), 8.00 (dd, 1H, J=7.5, 1.5 Hz), 7.17 (dd, 1H, J=7.5, 5.1 Hz). MS (+ve ES) 293 (28), (M+H) 147 (100). | |
In tert-butyl alcohol; | a 3,3-Dibromo-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one A solution of pyrrolo[2,3-b]pyridine (4.0 g, 34 mmol) in tert-BuOH (200 mL) was stirred at room temperature and <strong>[39416-48-3]pyridinium perbromide</strong> (32.5 g, 0.1 mol) was added in portions over 30 min, and the reaction mixture was stirred for 3 h. Pyridinium perbromide (10.8 g, 33 mmol) was added, and the mixture was stirred for a further 2 h. The tert-BuOH was evaporated under reduced pressure, and the residue was partitioned between water (300 mL) and EtOAc (300 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water (2*50 mL) and brine. The organic layer was dried over anhydrous MgSO4 and filtered, and the solvent was evaporated. Trituration of the residue with CH2Cl2 gave a white solid which was collected by filtration and dried under vacuum to provide 8.35 g of the title compound. 1H NMR (d6-DMSO) delta 11.99 (s, 1H), 8.21 (dd, 1H, J=5.1, 1.5 Hz), 8.00 (dd, 1H, J=7.5, 1.5 Hz), 7.17 (dd, 1H, J=7.5, 5.1 Hz). MS (+ve ES) 293 (28), (M+H) 147 (100). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; ethyl acetate; tert-butyl alcohol; | a 3,3-Dibromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one To a stirred solution of 1.32 g (8.7 mmol) of <strong>[55052-27-2]6-chloro-1H-pyrrolo[2,3-b]pyridine</strong> (Minakata et al., Synthesis 1992, 661-663) in tert-butanol (80 mL) was added 9.9 g (28 mmol) of 90% pyridine hydrobromide perbromide, resulting in immediate formation of a thick yellow precipitate. The reaction was concentrated, and the crude residue was chromatographed on silica gel, eluding with a hexane to 90% hexane/10% EtOAc gradient, to give 2.36 g of the title compound as white solid [1H NMR (CDCl3): delta7.16 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 9.0 (bs, 1H)] containing about 30% of 3,3,5-tribromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one as an inseparable impurity [1H NMR delta8.05 (s, 1H), 9.0 (bs, 1H)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In hexane; ethyl acetate; tert-butyl alcohol; | a 6-Chloro-7-aza-3,3-dibromooxindole <strong>[55052-27-2]6-Chloro-7-azaindole</strong> was prepared according to the procedure of Minakata et al; Synthesis, 1992, 661-663. To a stirred solution of 1.32 g (8.7 mmol) of <strong>[55052-27-2]6-chloro-7-azaindole</strong> in tert-butanol (80 mL) was added 9.9 g (28 mmol) of 90% pyridine hydrobromide perbromide reulting in a thick yellow precipitate forming immediately. The reaction was concentrated and the crude chromatographed on silica gel eluding with hexane to 90% hexane/10% EtOAc gradient to give 2.36 g of the title compound as a white solid, containing about 30% of 5-bromo-6-chloro-7-aza-3,3-dibromooxindole as an inseparable impurity. 1H NMR (CDCl3) delta7.16 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 9.0 (bs, 1H). | |
In hexane; ethyl acetate; tert-butyl alcohol; | a 3,3-Dibromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one To a stirred solution of 1.32 g (8.7 mmol) of <strong>[55052-27-2]6-chloro-1H-pyrrolo[2,3-b]pyridine</strong> (Minakata et al., Synthesis 1992, 661-663) in tert-butanol (80 mL) was added 9.9 g (28 mmol) of 90% pyridine hydrobromide perbromide, resulting in immediate formation of a thick yellow precipitate. The reaction was concentrated, and the crude residue was chromatographed on silica gel, eluding with a hexane to 90% hexane/10% EtOAc gradient, to give 2.36 g of the title compound as a white solid [1H NMR (CDCl3): delta 7.16 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 9.0 (bs, 1H)] containing about 30% of 3,3,5-tribromo-6-chloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one as an inseparable impurity [1H NMR delta 8.05 (s, 1H), 9.0 (bs, 1H)]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step A: 3,4,5,6-tetrahydrophthalimido-methyl (1R,cis) 2,2-dimethyl-3-(1,3-dibromo-2-oxopropyl)-cyclopropane-1-carboxylate. 0.8 g of 3,4,5,6-tetrahydrophthalimido-methyl (1R,cis) 2,2-dimethyl-3-(2-oxopropyl)-cyclopropane-1-carboxylate and 8 ml of tetrahydrofuran were mixed together under an inert gas atmosphere and then 1.72 g of pyridinium perbromide in the form of hydrobromide were added slowly. After 6 hours of stirring at +5 C., the precipitate was separated off and washed with tetrahydrofuran. Then, the filtrate was concentrated to dryness at 25 C. under reduced pressure, and the residue was chromatographed on silica, eluding with methylene chloride to obtain 0.31 g of the expected product. NMR Spectrum (CDCl3 250 MHz ppm): 1.22 (s), 1.19 (s), 1.25 (s) and 1.30 (s): twinned CH3; 1.76 (d) and 1.34 (m): H1 and H3; 1.78 (m): CH2 in beta position and 2.38 (m) CH2 in alpha position in the tetrahydro-phthalimide ring; 4.07 (d), 4.36 (d) and 4.28 (AB system): --COCH2 Br; 5.22 (d), 5.55 (d) and 5.57 (AB system): --CO2 CH2 --; 5.40 (d) and 5.42 (d): --COCHBr--. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.7% | In pyridine; | b) 17alpha-Ethinyl-17beta-hydroxy-13-methyl-gona-4,9-dien-3-one 15 g of 17alpha-ethinyl-17beta-hydroxy-13-methyl-gon-5(10)-en-3-one is dissolved in 219 ml of pyridine and mixed all at once with 18.6 g of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> with cooling (-5 C.). After 15 minutes, the cooling is removed and the solution slowly warming to room temperature is stirred for about 15 more minutes and then 2 ml of methyl butene is added to decompose the excess bromation agent. Then it is stirred for 5 hours at room temperature and the stirred into ice water to which some hydrochloric acid has been previously added. After crystallization, the steroid is suctioned off and optionally crystallized from ether. 14 g of tile dienone (92.7% of theory) is obtained. Mp: crude product: 168 C. to 173 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; water; | e) 17beta-hydroxy-16alpha,17alpha-methylene-estra-4,9-dien-3-one 2.3 g of 17beta-hydroxy-16alpha,17alpha-methylene-estr-5(10)-en-3-one is dissolved in 20 ml of pyridine dried on KOH and is mixed at -30 C. with stirring in an inert gas atmosphere with 2.88 g of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong>. Then, it is stirred for about 15 minutes at a temperature of about -5 C. and then the excess bromation agent is destroyed by addition of dihydropyrane. Then, it is stirred for 4 hours at room temperature, the reaction mixture is mixed with water and the steroid is extracted with methylene chloride. After the concentration of the extracts by evaporation, the remaining residue is chromatographed on silica gel. A benzene/ethyl acetate mixture (5:1 to 2:1) is used as mobile phase. 1.6 g of dienone, which can be crystallized from aqueous methanol, is obtained. Melting point: 191 C. to 193 C., [alpha]D =139.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; dimethyl amine; In dichloromethane; | 2-Dimethylaminomethyl-6-methyl-(E)-4(-2(2-carboxyethenyl)phenyl)-1,4-dihydro-3,5-pyridinedicarboxylic acid diethylester, hydrobromide (1) Method (A) Pyridine hydrobromide perbromide was added to a solution of (E)-4(-2(2-carboxyethenyl)phenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid diethyl ester (3.5 g) and pyridine (2 ml) in dichloromethane (100 ml) at 0 C. and stirred at the same temperature for 30 mins. The mixture was then cooled to -10 C. and dimethylamine (10.6 ml) was slowly added. The mixture was stirred at -10 C. for 1 hour. The solvent was then evaporated and the residue taken up with methanol to yield the title compound as a yellow solid, which was recrystallized from petrol ether/methanol (8:2) (2.7 g), m.p. 145-150 C. (dec). T.l.c. (CH2 Cl2 /Methanol, 8:2) Rf.=0.50 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation 69To the stirring solution of 6- [2-(3-methylphenyl) -2- oxoethyl]-3(2H) -pyridazinone (16 g) in ethyl acetate (240 mli) and AcOH (3.2 mL) was added <strong>[39416-48-3]pyridinium tribromide</strong> (24.7 g) at 50C. After 0.5 h, ethyl acetate and NaCO3aq were added and the mixture was extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated. The residue was dissolved in EtOH (240 mL) and to this was added thiourea (5.34 g) and the mixture warmed to 800C. After Ih, the reaction mixture was neutralized with NaHCO3 aq and EPO <DP n="55"/>concentrated. Water was added and the mixture was filtered to give 6- [2-amino-4-(3-methylphenyl) -1,3-thiazol-S- yl] -3(2H) -pyridazinone (17 g). Mass ESI(+) 285(M+1) 1H NMR (DMSO-d6,d) : 2.31(3H, s), 6.66(1H, d, J= 9.5 Hz), 6.87(1H, d, J= 9.5 Hz) , , 7.15-7.35(4H, m) , 7.4Q(2H, br s), 12.93(1H, br s) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In hexane; dichloromethane; | P.7: Preparation of 1-(3,4-dimethoxyphenyl)-6-chloro-2-bromo-3,4-dihydronaphthalene (intermediate). STR34 30.0 g of 1-(3,4-dimethoxyphenyl)-6-chloro-3,4-dihydronaphthalene are dissolved in 200 ml of methylene chloride and the solution is cooled to 0. 31.2 g of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> are added in portions thereto over a period of 11/2 hours at from 0 to 5. When the addition is complete, the violet solution is stirred for 2 hours at 0, 300 ml of 10% sodium bicarbonate solution are then added thereto, and the organic phase is separated off and washed with water, dried over sodium sulfate, filtered and concentrated by evaporation. The semi-crystalline product so obtained can be further reacted directly. Upon being left to stand for a longer period, the title compound crystallises out completely and can be digested in hexane. M.p. 92-95. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetic acid; | Step 1 [1R,3R] 8-Bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran A solution of 0.94 g (3.8 mmol) of 1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran, the product of Step 3 of Example 89 in 10 mL of glacial acetic acid was treated with a solution of 1.2 g (3.8 mmol) of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> in 50 mL of glacial acetic acid and the resultant mixture was stirred for 48 h at ambient temperature. The precipitate was filtered to afford 351 mg (28% yield) of the title compound. An additional 229 mg (18% yield) of the desired product precipitated from the filtrate after concentration in vacuo, to give a total of 580 mg (46% yield) of [1R,3R] 8-bromo-1-cyano-3,4-dihydro-5-hydroxy-3-phenyl-1H-2-benzopyran. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10.0 g of 16alpha-ethyl-3-methoxy-1,3,5(10)-estratrien-17beta-ol is subjected analogously to 1(e) in succession to Birch reduction, acid hydrolysis, and reaction with <strong>[39416-48-3]pyridine hydrobromide perbromide</strong>, thus obtaining 7.8 g of 16alpha-ethyl-17beta-hydroxy-4,9(10)-estradien-3-one, m.p. 132-135 C. (from ethyl acetate/diisopropyl ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
REFERENCE EXAMPLE 13 In 70 ml. of acetate acid is dissolved 4.7 g. of 6-benzyloxy-5-cyano-3,4-dihydro-1(2H)-naphthalenone and, under stirring at room temperature, 5.4 g. of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> (C5 H5 N. NBr. Br2) is added. The mixture is stirred at room temperature for 3 hours, after which time the acetic acid is distilled off under reduced pressure. The residue is shaken well with water and acetic acid. The ethyl acetate layer is taken, washed with water and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is crystallized from ethyl acetate-n-hexane. The procedure yields 4.9 g. of 6-benzyloxy-2-bromo-5-cyano-3,4-dihydro-1-(2H)-naphthalenone as colorless needles melting at 115-116 C. Elemental analysis: for C18 H14 O2 NBr; Calculated C, 60.69; H, 3.96; N, 3.93; Found C, 60.90; H, 3.81; N, 3.80. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; | a) Methyl 4-Bromo-2,5-dimethyl-1H-pyrrole-3-carboxylate A stirred solution of methyl 2,5-dimethyl-1H-pyrrole -3-carboxylate (1.5g, 9.8mmol) in chloroform (60ml) and triethylamine (2.5ml) cooled to 0C was treated portionwise with pyridinium perbromide (3.5g, 10.94 mmol). The mixture was allowed to warm to room temperature and then silica (6g) was added in one portion and the entire mixture evaporated to dryness under reduced pressure (14 mm Hg) with gentle heating (below 50). Chromatography on silica eluding with ethyl acetate-hexane mixtures gave the sub-title compound (1.9g), M+231/233. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In chloroform; water; tert-butyl alcohol; | A. 4-Cyano-3,3-dibromo-1,3-dihydro-1H-indol-2-one 1H-Indole-4-carbonitrile (prepared according to Clark, Robin D.; Repke, David B. J. Heterocycl. Chem. 1985,22, 121-5; 3.26 g, 22.9 mmol) was dissolved in a 3:1 mixture of tBuOH/H2O (100 mL). Pyridinium perbromide (25.6 g, 80.1 mmol) was then added to the stirring mixture in portions over 30 min. The mixture was stirred for 1 h and then the mixture was made neutral by the addition of sat. aq. NaHCO3. The mixture was stirred for an additional 2 h and the product was filtered off. A further portion of <strong>[39416-48-3]pyridinium perbromide</strong> (7.3 g, 22.9 mmol) was added to the filtrate, the resulting mixture was stirred overnight, and a further quantity of the product was filtered off. The filtrate was concentrated and the black residue was partially dissolved in CHCl3. It was filtered through a plug of silica gel which was flushed several times with warm chloroform. The solids collected from the filtrations were combined and purified in the same manner. 4-Cyano-3,3-dibromo-1,3-dihydro-1H-indol-2-one was obtained as a light brown solid (5.20 g, 72%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; | 3.1. Ethyl 3-bromoindole-7-carboxylate 12 g of <strong>[39416-48-3]pyridine hydrobromide perbromide</strong> are added to a solution of 5 g of ethyl indole-7-carboxylate in 50 g of pyridine. The reaction mixture is warmed to 30-50 and stirred until the conversion is complete (from about 3 to 10 hours). Conventional work-up gives ethyl 3-bromoindole-7-carboxylate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; for 1.66667h; | 1-(1-acetyl-2,3-dihvdro-1H-indol-5-yl)-2-bromoethanoneTo a suspension of 1 ,5-diacetylindoline (10.0 g, 49.2 mmol) in 90 mL of THF at rt was added <strong>[39416-48-3]pyridinium tribromide</strong> (16.52 g, 51 .7 mmol, 1 equiv) as solids portionwise over a period of 10 min. When there was still about 1.5 g of pyridinium trtibromide left, the mixture solidified. Added another 30 mL of THF to make the mixture stirrable again. The remaining 1.5 g tribromide was added in one portion. The mixture was stired at rt (no exotherm as checked by a thermometer). After 1 .5 h, LCMS showed conversion complete. The suspension was filtered. The cake was washed with THF (2x 30 mL), and then water (2x 50 mL).The wet cake was sucked under house vacuum at rt for 2 days to give 1 -(1 - acetyl-2,3-dihydro-1 H-indol-5-yl)-2-bromoethanone (12.89 g) as light grey solids. LC-MS (ES) m/z = 281.9, 283.9. |
Tags: 39416-48-3 synthesis path| 39416-48-3 SDS| 39416-48-3 COA| 39416-48-3 purity| 39416-48-3 application| 39416-48-3 NMR| 39416-48-3 COA| 39416-48-3 structure
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