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CAS No. : | 183208-35-7 |
Formula : | C7H5BrN2 |
M.W : | 197.03 |
SMILES Code : | BrC1=CN=C(NC=C2)C2=C1 |
MDL No. : | MFCD06659677 |
InChI Key : | LPTVWZSQAIDCEB-UHFFFAOYSA-N |
Pubchem ID : | 10307932 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P261-P280-P305+P351+P338 |
* 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 |
---|---|---|
93% | at 20℃; for 6 h; | Step 1: Synthesis of 1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone. To a stirring solution of aluminum chloride (6.77 g, 50.75 mmol) suspended in anhydrous CH2Cl2 (100 mL) under N2 was added 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.00 g, 10.15 mmol). The reaction solution was stirred for 1 hour at ambient temperature whereupon acetyl chloride (3.61 mL, 50.75 mmol) was added dropwise and the resulting solution was stirred for 5 more hours. The reaction was cooled to 0° C. in an ice bath and quenched carefully by addition of MeOH until the solution became clear. The reaction was concentrated under vacuum. H2O was added and 1 N NaOH was added dropwise until the pH=4. The product was extracted into ethyl acetate and the organic layer was washed with a saturated solution of sodium potassium tartrate to remove any remaining aluminum salts. The organic layer was dried over Na2SO4 and concentrated under vacuum. The material was redissolved in ethyl acetate and filtered through a bed of silica gel. The filtrate was concentrated to afford the title compound as an orange solid (2.25 g, 93percent yield). 1H NMR (500 MHz, d6-DMSO) δ 12.70 (br s, 1H), 8.56 (d, J=2.5 Hz, 1H), 8.55 (s, 1H), 8.40 (d, J=2.5 Hz, 1H), 2.46 (s, 3H). MS: m/z 238.9/240.9 (M+H+). |
93% | Stage #1: With aluminum (III) chloride In dichloromethane at 20℃; for 1 h; Stage #2: for 5 h; | To a stirring solution of aluminum chloride (6.77 g, 50.75 mmol) suspended in anhydrous CH2Cl2 (100 mL) under N2 was added 5-bromo-1H -pyrrolo[2,3-δ]pyridine (2.00 g, 10.15 mmol). The reaction solution was stirred for 1 hour at ambient temperature whereupon acetyl chloride (3.61 mL, 50.75 mmol) was added dropwise and the resulting solution was stirred for 5 more hours. The reaction was cooled to 0 °C in an ice bath and quenched carefully by addition of MeOH until the solution became clear. The reaction was concentrated under vacuum. H2O was added and 1 N NaOH was added dropwise until the pH = 4. The product was extracted into ethyl acetate and the organic layer was washed with a saturated solution of sodium potassium tartrate to remove any remaining aluminum salts. The organic layer was dried over Na2SO* and concentrated under vacuum. The material was redissolved in ethyl acetate and filtered through a bed of silica gel. The filtrate was concentrated to afford the title compound as an orange <n="79"/>solid (2.25 g, 93percent yield). 1H NMR (500 MHz, ^-DMSO) δ 12.70 (br s, 1H), 8.56 (d, J = 2.5 Hz, 1H),8.55 (s, 1H), 8.40 (d, J = 2.5 Hz, 1H), 2.46 (s, 3H). MS: m/z 238.9/240.9 (M + H+). |
87% | Stage #1: With aluminum (III) chloride In dichloromethane at 20℃; for 1 h; Stage #2: at 20℃; | 5-Bromo-1H-pyrrolo[2,3-b]pyridine (5 g, 25.2 mmol) was added to aluminum chloride (16.8 g, 126.2 mmol) in dichloromethane (200 ml) under nitrogen. The mixture was allowed to stir at room temperature for 1 hour. Acetyl chloride (9 ml, 126.2 mmol) in dichloromethane was added drop wise and the reaction was allowed to proceed at room temperature overnight. Next day the reaction was cooled to 0° C. and quenched with methanol (500 ml) until the reaction turned clear. The reaction was concentrated under vacuum and resuspended in water (300 ml). The pH was adjusted to 4 with 7N sodium hydroxide solution and then extracted with ethyl acetate (300 ml.x.3). The combined organic layers were extracted with saturated sodium potassium tartrate and brine and dried with Na2SO4. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 1-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-ethanone (5.2 g, 87percent yield). 1H NMR (500 MHz, DMSO-d6) δ 2.48 (s, 3H), 8.41 (s, 1H), 8.57 (s, 1H), 8.58 (s, 1H). MS: m/z 241.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With N-chloro-succinimide; dibenzoyl peroxide In N,N-dimethyl-formamide at 20℃; for 18 h; | 0.50 g (2.54 mmol) of 5-bromo-lH-pyrrolo[2,3-b]pyridine was dissolved in 10 n L of Ν,Ν-dimethylformamide to which 0.37 g (2.79 mmol) of N-cMorosuccinimide and 0.38 g (2.79 mmol) of dibenzoyl peroxide were added, followed by stirring at room temperature for 18 hours. After extracting with ethyl acetate/distilled water, the organic layer was concentrated under reduced pressure. The residue was separated by column chromatography to give 0.50 g (85.0percent yield) of 5-bromo-3-chloro-lH-pyrrolo[2,3-b] pyridine. 1H NMR (DMSO) δ: 12.24 (br s, 1H), 8.35 (s, 1H), 8.14 (s, 1H), 8.03 (d, 1H), 7.81 (m, 1H), 7.77 (s, 1H), 7.64 (t, 1H) |
85% | With N-chloro-succinimide In tetrahydrofuran at 20℃; for 24 h; | 5 -Bromo-3 -chloro- 1H-pyrrolo[2,3 -bipyridine. To a solution of 5 -bromo- 1H-pyrrolo [2,3 -bjpyridine (5.0 g, 25.4 mmol, 1.0 eq) in THF (100 mL) was added N-chlorosuccinimide (4.0 g,30.4 mmol, 1.2 eq) and the mixture was stirred at room temperature for 24 h. Water (100 mL)was added to the reaction mixture, followed by extraction with EA (3 x 80 mL). The combinedorganic layer was dried over Mg2SO4, filtered and the filtrate was concentrated in vacuo to givea cmde residue, which was purified by silica gel column chromatography (EtOAc/Hexane, 1/5)to afford 5-bromo-3-chloro-1H-pyrrolo[2,3-bjpyridine (5.0 g, 85percent). ‘H NMR (300 MHz,DMSO-d6): 5 12.26 (br, 1H), 8.37 (s, 1H), 8.16 (s, 1H), 7.79 (s, 1H). ESI-MS (m/z): 232.9 (M-t-H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | aluminum (III) chloride; In dichloromethane; at 20℃; for 6h; | Step 1: Synthesis of 1-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone. To a stirring solution of aluminum chloride (6.77 g, 50.75 mmol) suspended in anhydrous CH2Cl2 (100 mL) under N2 was added 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.00 g, 10.15 mmol). The reaction solution was stirred for 1 hour at ambient temperature whereupon acetyl chloride (3.61 mL, 50.75 mmol) was added dropwise and the resulting solution was stirred for 5 more hours. The reaction was cooled to 0 C. in an ice bath and quenched carefully by addition of MeOH until the solution became clear. The reaction was concentrated under vacuum. H2O was added and 1 N NaOH was added dropwise until the pH=4. The product was extracted into ethyl acetate and the organic layer was washed with a saturated solution of sodium potassium tartrate to remove any remaining aluminum salts. The organic layer was dried over Na2SO4 and concentrated under vacuum. The material was redissolved in ethyl acetate and filtered through a bed of silica gel. The filtrate was concentrated to afford the title compound as an orange solid (2.25 g, 93% yield). 1H NMR (500 MHz, d6-DMSO) delta 12.70 (br s, 1H), 8.56 (d, J=2.5 Hz, 1H), 8.55 (s, 1H), 8.40 (d, J=2.5 Hz, 1H), 2.46 (s, 3H). MS: m/z 238.9/240.9 (M+H+). |
93% | To a stirring solution of aluminum chloride (6.77 g, 50.75 mmol) suspended in anhydrous CH2Cl2 (100 mL) under N2 was added 5-bromo-1H -pyrrolo[2,3-delta]pyridine (2.00 g, 10.15 mmol). The reaction solution was stirred for 1 hour at ambient temperature whereupon acetyl chloride (3.61 mL, 50.75 mmol) was added dropwise and the resulting solution was stirred for 5 more hours. The reaction was cooled to 0 C in an ice bath and quenched carefully by addition of MeOH until the solution became clear. The reaction was concentrated under vacuum. H2O was added and 1 N NaOH was added dropwise until the pH = 4. The product was extracted into ethyl acetate and the organic layer was washed with a saturated solution of sodium potassium tartrate to remove any remaining aluminum salts. The organic layer was dried over Na2SO* and concentrated under vacuum. The material was redissolved in ethyl acetate and filtered through a bed of silica gel. The filtrate was concentrated to afford the title compound as an orange <n="79"/>solid (2.25 g, 93% yield). 1H NMR (500 MHz, ^-DMSO) delta 12.70 (br s, 1H), 8.56 (d, J = 2.5 Hz, 1H),8.55 (s, 1H), 8.40 (d, J = 2.5 Hz, 1H), 2.46 (s, 3H). MS: m/z 238.9/240.9 (M + H+). | |
87% | 5-Bromo-1H-pyrrolo[2,3-b]pyridine (5 g, 25.2 mmol) was added to aluminum chloride (16.8 g, 126.2 mmol) in dichloromethane (200 ml) under nitrogen. The mixture was allowed to stir at room temperature for 1 hour. Acetyl chloride (9 ml, 126.2 mmol) in dichloromethane was added drop wise and the reaction was allowed to proceed at room temperature overnight. Next day the reaction was cooled to 0 C. and quenched with methanol (500 ml) until the reaction turned clear. The reaction was concentrated under vacuum and resuspended in water (300 ml). The pH was adjusted to 4 with 7N sodium hydroxide solution and then extracted with ethyl acetate (300 ml×3). The combined organic layers were extracted with saturated sodium potassium tartrate and brine and dried with Na2SO4. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 1-(5-bromo-1H-pyrrolo[2,3-b]pyridine-3-yl)-ethanone (5.2 g, 87% yield). 1H NMR (500 MHz, DMSO-d6) delta 2.48 (s, 3H), 8.41 (s, 1H), 8.57 (s, 1H), 8.58 (s, 1H). MS: m/z 241.0 (M+H+). |
Aluminum trichloride (846 mg) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (250 mg) in dichloromethane (5 ml) at room temperature over 10 minutes. Subsequently, acetyl chloride (135 mul) was added and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into ice-cold water and separated by adding dichloromethane. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with methanol-chloroform) to give the title compound (186 mg).MS (ESI) m/z: 239 (M+H)+.1H-NMR (CDCl3) delta: 2.55 (3H, s), 7.98 (1H, d, J=2.8 Hz), 8.45 (1H, d, J=2.3 Hz), 8.85 (1H, d, J=1.8 Hz), 10.28 (1H, br s). | ||
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃;Inert atmosphere; | To a soluition of 5-bromo-lH-pyrrolo[2,3-b]pyridine(30 g, 0.15 mol) and aluminium chloride (100 g, 0.75 mol) in dichloromethane (2000 mL) was added dropwise acetyl chloride (102 mL, 1.44 mol) over 1 h under nitrogen atmosphere at 0 C. The reaction mixture was warmed to RT and stirred overnight. Methanol (150 mL) was added dropwise at 0 C, and the resulting mixture was concentrated to dryness in vacuo. The resulting crude was dissolved in ice -water, basified with saturated sodium bicarbonate to pH 4 - 5 and extracted with ethyl acetated (3 x 3000 mL). The combined organic layer were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as a yellow solid (330 g, 93 % after 10 batch repeat) used for the next step without any further purification: NMR (DMSO, 400 MHz): delta 12.675 (s, 1H), 8.537-8.543 (d, J = 2.4 Hz, 1H), 8.506 (s, 1H), 8.371-8.377 (d, J = 2.4 Hz, 1H), 2.445 (s, 3H). | |
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃;Inert atmosphere; | Preparative Example 6 Step 1: l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone To a soluition of 5-bromo-lH-pyrrolo[2,3-b]pyridine(30 g, 0.15 mol) and aluminium chloride (100 g, 0.75 mol) in dichloromethane (2000 mL) was added dropwise acetyl chloride (102 mL, 1.44 mol) over 1 h under nitrogen atmosphere at 0 C. The reaction mixture was warmed to RT and stirred overnight. Methanol (150 mL) was added dropwise at 0 C, and the resulting mixture was concentrated to dryness in vacuo. The resulting crude was dissolved in ice -water, basified with saturated sodium bicarbonate to pH 4 - 5 and extracted with ethyl acetated (3 x 3000 mL). The combined organic layer were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as a yellow solid (330 g, 93 % after 10 batch repeat) used for the next step without any further purification: lH NMR (DMSO, 400 MHz): delta 12.675 (s, 1H), 8.537-8.543 (d, = 2.4 Hz, 1H), 8.506 (s, 1H), 8.371- 8.377 (d, J = 2.4 Hz, 1H), 2.445 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | 5-Bromo-li/-pyrrolo[2,3-6]pyridine (1 g, 5.075 mmol) was dissolved in DMF (8 mL) and cooled to 0 C. Then NaH (300 mg, 7.51 mmol, 60 % dispersion in mineral oil) was added, and the mixture was stirred for 20 minutes at room temperature. After cooling the mixture to 0 C, benzenesulfonyl chloride (0.78 mL, 6.09 mmol) was added dropwise, and allowed to warm to room temperature. After 2 hours reaction time, the mixture was treated with saturated NH4CI, extracted with CH2CI2 (2x). The combined organic layers were washed with water (2x) and brine, dried over NazSCL, and evaporated to dryness to give 1.71 g (100 %) of i-(benzenesulfonyl)-5-bromo-i//-pyrrolo[2,3-6]pyridine. | |
99.6% | To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine 17 (5 g, 25 mmol) in N,N-Dimethylformamide (DMF, 40 mL) Sodium hydride (NaH, 0.91 g, 37 mmol) was added at 0 C and stirred at 25 C for 20 min. To the mixture Benzenesulfonyl chloride (5.37 g, 30 mmol) was added dropwise at 0 C and stirred at 25 C for 1 h. The mixture was quenched with Ammonium chloride (NH4Cl) solution, extracted with Bichloromethane (DCM, 50 mL * 2). The organic phase was washed with water (50 mL * 2), brine (50 mL * 2), dried over Sodium sulfate (Na2SO4). After filtering, the organic phase was concentrated to give compound 18 as a white solid (8.5 g, 99.6% yield). 1H NMR (400 MHz, CDCl3) delta 8.44 (s, 1H, Ar-H), 8.18-8.16 (d, J = 7.8 Hz, 2H, Ar-H), 7.96 (s, 1H, Ar-H), 7.74-7.73 (m, J = 4.0 Hz, 1H, Ar-H), 7.59-7.50 (t, J = 7.4 Hz, 1H, Ar-H), 7.47-7.38 (t, 2H, Ar-H), 6.55-6.54 (d, J = 4.0 Hz, 1H, Ar-H). | |
95% | A solution of 5-bromo- lH-pyrrolo[2,3-b]pyridine 8 (196 g, 994 mmol) in anhydrous tetrahydrofuran (2 L) was cooled to 0 C and treated with sodium hydride (60% in mineral oil, 49.3 g 1233 mmol) over 30 minutes. After two hours, benzenesulfonyl chloride 9 (153 mL, 1 193 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The reaction was quenched with brine (1 L). The layers were separated and the aqueous phase was extracted with ethyl acetate (2 x 500 mL). The organic layers were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure. The product was triturated with methyl tert-butyl ether to give compound 10 as a tan solid (319 g, 95%). The data from the lH NMR spectrum were consistent with the structure of the compound. |
94.3 - 94.8% | Preparation of 5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (B-7-4)B-7-3 B-7-4To a suspension of 5-bromo-1 H-pyrrolo[2,3-b]pyridine (B-7-3) (6.2 g, 0.031 mol) in THF (100 mL) was added NaH (1.51 g, 0.037 mol) under N2. BsCI (3.58 g, 0.035mol) was added 30 minutes later. The mixture was stirred at room temperature overnight. TLC (Petroleum ether: EtOAc = 5:1 ) showed that the reaction was complete. Water (200 mL) and EtOAc (50 mLchi3) were added into the mixture. The organic layer was separated and concentrated to give 5-bromo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (B-7- 4) (10 g, 94.3%) as a light yellow solid. 1HNMR (400 MHz, CDCI3): delta 8.465 (s, 1 H), 8.141-8.114 (d, 2H), 7.905 (s, 1 H), 7.679-7.669 (d, 1 H), 7.586-7.529 (m, 1 H), 7.430-7.351 (2, 1 H), 6.458-6.475 (d, 1 H). Example H-1 : 4-(3-(3-chloro-1 H-pyrrolo[2,3-b]pyridin-5-yl)-1 -isopropyl-1 H-pyrazol-4-yl)pyridin-2- aminePreparation of 5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (H-1 -2)H-1-1 H-1 -2To a suspension of NaH (87 g, 2.18 mol, 60% in oil) in dry THF (1 L) was added dropwise a solution of 5- bromo-1 H-pyrrolo[2,3-b]pyridine H-1-1 (120 g, 0.62 mol) in dry THF (1 L) at O0C. After addition, the mixture was stirred at O0C under N2 for 0.5 h. To the mixture was added dropwise BsCI (219.5 g, 1.24 mol) at 50C. After the addition, the mixture was stirred at room temperature overnight. TLC (Petroleum ether/EtOAc 5:1 ) showed the reaction was complete. The reaction mixture was poured slowly into ice-cold saturated NH4CI (500 mL). The mixture was extracted with EtOAc (600 mLchi2). The combined organic layers were washed with saturated aqueous NaCI (700 mL), dried over Na2SO4 and concentrated in vacuo. The residue was washed with Petroleum ether/EtOAc (15:1 , 1.5 L) to give compound H-1-2 (198 g, 94.8%) as an off-white solid. | |
92.2% | With pyridine; at 85℃; for 4h; | Compound numbers 1 to 7 recited in Example 4 apply only to Example 4. To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridine(50 g, 0.254 mol) in pyridine (300 mL) was added benzene sulfonyl chloride (224 g, 1.27 mol). The resulted mixture was heated at 85 C for 4 hours and then concentrated under vacuum. The residue was diluted with EtOAc (1500 mL). The pH of the solution was adjusted to 3 with 1M HC1, and the resulted mixture was washed with NaHC03 and water. The organic layer was washed with water and brine, dried (Na2S04) and concentrated. The residue was purified by a silica gel column to afford (85 g, 99.2 %) of the title compound as a slightly yellow solid |
76% | 5-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine To a well stirred solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 50.7 mmol) in dry THF (100 mL) was added NaH (60% oil suspension; 3.0 g, 75 mmol) at 0 C. and stirred for 30 min. Phenylsulfonyl chloride (10.7 g, 60 mmol) was added slowly and the mixture was stirred at ambient temperature for 16 h (TLC monitoring: 60% ethyl acetate in hexanes). Solvent was removed under reduced pressure, water (25 mL) was added to the residue, and the mixture was extracted with dichloromethane (3*100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue thus obtained was crystallized from dichloromethane to yield the title compound (13.0 g, 76%). 1H NMR (CDCl3, 300 MHz): delta=6.55 (d, J=4.2 Hz, 1H), 7.46-7.62 (m, 3H), 7.74 (d, J=4.0 Hz, 1H), 7.97 (d, J=2.1 Hz, 1H), 8.15-8.18 (m, 2H), 8.44 (d, J=2.1 Hz, 1H). | |
75% | With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 0℃; for 2h; | Preparation of Method A Intermediate 2: l-Benzenesulfonyl-5-bromo-lH-pyrrolo[2,3- b] pyridine[0425] 5-Bromoazaindole (1, 2.00 g, 10.1 mmol), tetrabutylammonium bromide (0.03 eq, 0.25 mmol, 82 mg) and powdered NaOH (3 eq, 30.45 mmol, 1.22 g) are combined in DCM (100 ml) and cooled to 0C. Phenylsulfonyl chloride (1.25 eq, 12.69 mmol, 1.62 mL) is added dropwise. After the addition is completed the mixture is stirred for 2h at 0C. The mixture is filtered, absorbed on Celite and purified by silica gel chromatography with a 40 to 60% gradient of EtOAc in hexane. 2.58 g (7.65 mmol, 75% yield) of 2 is obtained. 1H NMR (CDC13, 300 MHz): delta 8.45 (d, J= 1.8 Hz, 1H), 8.17 (m, 2 H), 7.98 (d, J= 2.1 Hz, 1H), 7.74 (d, J= 3.9 Hz, 1H), 7.60 (m, 1H), 7.50 (m, 2H), 6.55 (d, J= 3.9 Hz, 1H). MS (m/z): 338 (M+H). |
75% | With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 0℃; for 2h; | 5-Bromoazaindole (1, 2.00 g, 10.1 mmol), tetrabutylammonium bromide (0.03 eq, 0.25 mmol, 82 mg) and powdered NaOH (3 eq, 30.45 mmol, 1.22 g) are combined in DCM (100 ml) and cooled to 0C. Phenylsulfonyl chloride (1.25 eq, 12.69 mmol, 1.62 mL) is added dropwise. After the addition is completed the mixture is stirred for 2h at 0C. The mixture is filtered, absorbed on Celite and purified by silica gel chromatography with a 40 to 60% gradient of EtOAc in hexane. 2.58 g (7.65 mmol, 75% yield) of 2 is obtained. XH NMR (CDC13, 300 MHz): delta 8.45 (d, J= 1.8 Hz, 1H), 8.17 (m, 2 H), 7.98 (d, J= 2.1 Hz, 1H), 7.74 (d, J= 3.9 Hz, 1H), 7.60 (m, 1H), 7.50 (m, 2H), 6.55 (d, J= 3.9 Hz, 1H). MS (m/z): 338 (M+H). |
55.46% | To a mixture of 5-bromo-7-azaindole (1.00 g, 5.08 mmol) and DMF (3 ml) was added 60% NaH (0.13 g, 5.59 mmol). The mixture was stirred for 10 minutes, and, after addition of benzenesulfonyl chloride (0.71 ml, 5.59 mmol), was stirred again overnight at room temperature. The reaction was quenched with water and the mixture was extracted with ethyl acetate (30ml x 3). The organic layer was collected, dried over anhydrous MgS04, and concentrated in vacuo to yield a brown residue, which was purified by a flash column over silica gel (ethyl acetate: n-hexane = 1 : 1, Rf = 0.40) to afford 11a (0.95 g, 55.46%) as a yellow solid. *H-NMR (500MHZ, CDCI3 ): delta 6.55 (d, /= 4.5 Hz, 1H), 7.50 (t, /= 8.0 Hz, 2H), 7.59(t, /= 7.5 Hz, 1H), 7.74 (d, /= 4.0 Hz, 1H), 7.97 (d, /= 2.0Hz, 1H), 8.17 (t, /= 8.0 Hz, 2H), 8.45 (d, /= 2.0Hz, 1H). | |
EXAMPLE 1; Compound 1-1; 5-?-methyl-lH-pyrazol-4-yl)-3-(6-piperazin-l-ylpyrazin-2-v?-lH-pyrrolor2,3-b1pyridine; Step 1 : 5-bromo-l-(phenylsulfonylMH-pyrrolo[2,3-fr]rhoyridine; To a stirred solution of 5-bromo-lH-pyrrolo[2,3-Z>]pyridine (20.0 g, 102 mmol) in DMF (400 ml) at 0 0C was added NaH (60% mineral oil dispersion; 4.87 g, 122 mmol) slowly (CAUTION: GAS EVOLUTION). The reaction mixture was stirred at 0 C for 2 h. Benzenesulfonyl chloride (17.0 ml, 132 mmol) was added dropwise, and the reaction mixture was allowed to warm to ambient. After 1 hour the reaction mixture was cooled in an ice bath, and 100 mL of water was added slowly (CAUTION: GAS EVOLUTION, EXOTHERM). The reaction mixture was partitioned between ethyl acetate (500 mL) and brine (600 mL). The organic layer was washed with additional brine (500 mL), followed by saturated aqueous ammonium chloride (250 mL). The first and 3rd aqueous layers were combined and back- extracted with ethyl acetate (500 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to a thick slurry. EtOAc (100 mL) was added, followed by hexanes (100 mL). The mixture was filtered, and the filter cake was rinsed with 1 :1 EtOAc/Hexanes (50 mL) to afford 5-bromo-l-(phenylsulfonyl)-lH-pyrrolo[2,3-£]pyridine as a grey solid. The filtrate can be concentrated and purified by silica gel chromatography (EtOAc/etaexanes gradient) to afford additional product. LRMS (ESI) calculated for C13H9BrN2O2S [M+H]+, 337.0; found 336.9. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium tert-butylate; In N,N-dimethyl-formamide; at 60 - 85℃;Large scale; | Add 150 kg of DMF to a 200 L reactor, slowly add 70 kg of potassium t-butoxide, stir to 60-70 C, and slowly add 50 kg of <strong>[1210838-82-6]5-bromo-3-ethynyl-2-aminopyridine</strong>. The temperature control is not higher than 80 C , plus complete the reaction incubated 80-85 C 2 ~ 3h, TLC monitoring completion of the reaction (PE / DCM = 1/1), cooled after completion of the reaction, the reaction system was slowly added to 400kg of ice water, cooled to 10 C was stirred for 2h, filtered off with suction (suction Should difficult, adding an appropriate amount of filter aid such as diatomaceous earth, etc.), to give a brown solid crude wet weight of about 75 kg (about 95% HPLC purity). The wet product was added to a 500 L reaction vessel, 300 kg of ethyl acetate (EA) was added, 5 kg of activated carbon was added, and the mixture was heated under reflux for 30 minutes, and then suction filtered. The filter cake was washed with an appropriate amount of EA, and then the filtrate and the washing liquid were combined, and the EA was evaporated to about 250 kg under reduced pressure. (Remaining about 50kg in the kettle), cooling to 0-5 C for 2h, suction filtration, filter cake washed with appropriate amount of cold EA, blasting at 60 C to obtain a light yellow solid product 5-bromo-7-azaindole 45kg, yield 90%, HPLC purity 99.3% |
Example 7; a) Preparation of 5-bromo-7-azaindole (3 or Ia) from isolated 2-amino-5-bromo-3-iodopyridine; A suspension of 2-amino-5-bromo-3-iodopyridine (5.0 g, 16.7 mmol), bis-(triphenylphosphine)-palladium(II)-dichloride (43 mg, 0.061 mmol), copper(I)iodide (29.4 mg, 0.15 mmol) and triethylamine (2.21 g, 21.8 mmol) in dichloromethane (20 mL) was treated at 23 to 30 C. within 1 to 2 hours with a solution of 1,1-dimethyl-2-propyn-1-ol (1.85 g, 21.7 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at 25 C. for 4 hours. The mixture was diluted with dichloromethane (10 mL) and washed with water (2×25 mL). The organic phase was then treated with 1 M HCl (40 mL). The layers were separated and the organic layer was extracted with 1 M HCl (15 mL). The combined product containing aqueous layers were washed with dichloromethane (2×8 mL). The pH of the aqueous layer was adjusted to pH 7-9 by the drop wise addition of sodium hydroxide solution (28% in water). The resulting suspension was stirred at 20 C. over night and the crystals were then filtered off and washed with water (2×5 mL). The wet crystals were dissolved in N-methylpyrrolidone (50 mL) and treated within 2 hours at 60 C. and 50-100 mbar with an aqueous solution of lithium hydroxide (2.4 M, 32 mL). The resulting mixture was heated to 75 C. and stirred at this temperature and under reduced pressure (50-100 mbar) for 15-20 hours. Toluene (20 mL) and water (20 mL) were then added and the layers were separated. The aqueous layer was extracted with toluene (3×25 mL). The combined organic layers were washed with water (3×10 mL) and then concentrated to dryness. The residue was dissolved in N-methylpyrrolidone (50 mL) and treated at 60 C. with potassium tert.-butylate (3.52 g, 30.7 mmol). After stirring for 3 hours at 60 C., the mixture was cooled to ambient temperature and diluted with toluene (40 mL) and water (40 mL). The aqueous layer was separated and back extracted with toluene (3×50 mL). The combined toluene layers were washed with water (3×10 mL) and then concentrated to dryness. The residue was dissolved in a hot mixture of toluene and n-heptane (20 mL). The clear solution was cooled to -5 C. within 4 to 6 hours whereupon crystals precipitated. The suspension was stirred at -5 C. for 2-4 hours. The crystals were filtered off, washed with heptane and dried at 45 C./<30 mbars over night to afford 5-bromo-7-azaindole (2.05 g, 62% yield) as slightly yellow crystals with a purity of 99.6% (HPLC, area %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | step 1 : To a solution of 5-bromo-1H-pyrrolo[2,3-6]pyridine (2.0 g, 10 mmol) in anhydrous THF (50 mL) at -70 °C under nitrogen was added n-butyl lithium (2.5 M in hexane, 50 mmol) and the reaction mixture was stirred for 1 h at -70 °C. The resulting orange gel was quenched with methyl formate (10 mL) and the reaction mixture was slowly warmed to RT. The mixture was poured into water (20 mL) and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (Na2SO4), filtered, and concentrated to afford 500 mg, (33percent) of 1H-pyrrolo[2,3-6]pyridine-5-carbaldehyde as yellow solid. MS (ESI) m/z: 147.2 [M+l] +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | Under 2 atmosphere, 5-bromo-lH-pyrrolo [2, 3-j ] pyridine (1.66 g, 8.45 mmol, 1.20 equiv) was dissolved in DMF (35.2 mL, 0.240 M) and stirred at 0 °C. NaH (0.338g, 8.45 itunol, 1.20 equiv, 60 percent dispersion in mineral oil) was added in portionwise. After 30 min, 2-fluoro-5- nitropyridine (1.00 g, 7.04 mmol. 1.00 equiv) was added and then the reaction mixture was slowly warmed up to 60 'C and stirred at 60 °C 5 for 16 h. The reaction mixture was poured to a solution of LiCl (100 mL) , extracted with EtOAc. The combined organic layers washed with brine, dried (MgSO , filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with hexanes : EtOAc (20:1 to 10:1 (v/v) ) , to afford the title compound as 10 a yellow solid (1.26 g, 3.94 mmol, 56percent yield). Rf = 0.69 (hexanes: EtOAc 5:1 (v/v)). NMR Spectroscopy: XH NMR (500 MHz, CDC13, 25 °C, delta) : 9.31 (d, J= 2.58 Hz, 1H) , 9.30 (d, J = 9.04 Hz, 1H) , 8.64 (d, J = 2.58 Hz, 1H) , 8.62 (d, J = 2.58 Hz, 1H) , 8.49 (d, J = 4.30 Hz, 1H), 8.46 (d, J = 2.15 Hz, 1H) , 8.10 (d, J = 2.15 Hz, 1H) . 13C 15 NMR (175 MHz, CDC13, 25 °C, delta) : 153.8, 146.4, 144.9, 144.3, 141.1, 134.0, 131.9, 127.8, 125.8, 114.6, 114.4, 104.5. Mass Spectrometry: HRMS (ESI-TOF) (m/z) : calcd for C^HeBr ^ ( [M + H]+), 318.9825, found, 318.9826. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1.0 g, 5.0 mmol, 1.0 eq.) in anhydrous THF (50 mL) at -78° C. under argon was slowly added a solution of 1.6 M n-butyl lithium in hexane (6.7 mL, 10.7 mmol, 2.1 eq.) and the reaction mixture was allowed to stir for next 40 min at -78° C. To the resulting suspension 1 mL of dry DMF was added successively and the reaction mixture stirring was continued at rt overnight. Then the reaction mixture was quenched with saturated solution of NH4Cl; the organic layer was separated and the aqueous phase was extracted with EtOAc. The organic layers were combined, washed with brine, dried over Na2SO4, filtered and concentrated to afford 1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (Intermediate 3a) as an yellow solid (1.0 g; yield: 69percent; UPLC purity: 98percent). | |
1. To a solution of 5-bromo-lH-pyrrolo[2,3-b]pyridine (600 mg, 3.045 mmol) in 20 mL of THF, was added sodium hydride (60 wt dispersion, 146 mg, 3.65 mmol) at 0 °C. After 30 min, the reaction was added 4.38 mL of n-BuLi solution in hexanes (1.6 M) at -15 °C. After 1 hr at -15 °C, DMF (10 mL) was added and allowed to warm to RT. After 2 hr, the reaction was quenched with water, and extracted with EtOAc (x3). The combined organic extracts were washed with water (x2), dried (MgS04), and concentrated to give crude 1 H-pyrrolo [2, 3- b]pyridine-5-carbaldehyde (572.8 mg ). |
Tags: 5-Bromo-7-azaindole | Other Aromatic Heterocycles | Bromides | Pyrroles | Heterocyclic Building Blocks | Organic Building Blocks | 183208-35-7
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