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Chemical Structure| 619331-35-0 Chemical Structure| 619331-35-0

Structure of 619331-35-0

Chemical Structure| 619331-35-0

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Product Details of [ 619331-35-0 ]

CAS No. :619331-35-0
Formula : C8H7BrN2O
M.W : 227.06
SMILES Code : COC1=CN=C(Br)C2=C1C=CN2
MDL No. :MFCD12756855
InChI Key :SSEKUWDRHZZSFH-UHFFFAOYSA-N
Pubchem ID :20791244

Safety of [ 619331-35-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 619331-35-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 619331-35-0 ]

[ 619331-35-0 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 917918-80-0 ]
  • [ 619331-35-0 ]
YieldReaction ConditionsOperation in experiment
27% E1 7-Bromo-4-methoxy-6-azaindole To a flask containing 7-hydroxy-4-methoxy-6-azaindole (0.200 g, 1.22 mmol) was added anisole (3 mL) and then POBr3 (1.57 g, 6.09 mmol). The system was purged with Ar and then it was heated at 160 C. (oil bath temperature) for 1 h. The reaction mixture was then allowed to cool to room temperature, quenched with 2M HBr (5 mL) and extracted with methyl t-butyl ether. The aqueous phase was separated and the pH was adjusted to 6-7, after which it was extracted with EtOAc. The resulting organic phase was dried (MgSO4) and evaporated to give a solid residue which was chromatographed (SiO2/5% MeOH-DCM) to afford the title compound (0.076 g, 27%) as a white solid: LCMS m/e 227 (M+H)+.
  • 2
  • [ 5781-53-3 ]
  • [ 619331-35-0 ]
  • [ 954215-11-3 ]
YieldReaction ConditionsOperation in experiment
99% E2 Methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate To a solution of AlCl3 (0.587 g, 4.40 mmol) in DCM-MeNO2 (4:1, 3 mL) was added a solution of <strong>[619331-35-0]7-bromo-4-methoxy-6-azaindole</strong> (0.100 g, 0.440 mmol) in DCM-MeNO2 (4:1, 1 mL), followed by methyl oxalyl chloride (0.162 mL, 1.76 mmol). The resulting deep orange solution was stirred at room temperature for 1 h and then it was quenched by the slow addition of 1M NH4OH. The mixture was extracted with ethyl acetate (2*) and the combined organic phases were dried (MgSO4) and evaporated to give the title compound (0.136 g, 99%) as a white solid weighing: 1H-NMR (400 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.41 (d, J=3.0 Hz, 1H), 7.84 (s, 1H), 3.92 (s, 3H), 3.86 (s, 3H).
Process for the Preparation of Compound J-In-3 from J-In-2:[00149] To a stirred solution of aluminum chloride (4 eq.) in dry dichloromethane under nitrogen atmosphere was added J-In-2 (1 eq.) portion wise and the reaction mixture was stirred at room temperature for 2h. In a separate flask, to a stirred solution of aluminum chloride (6 eq.) in dry dichloromethane under nitrogen atmosphere was added methoxy oxalylchloride (3 eq.) drop wise. The reaction mixture was allowed to stir at room temperature for 2hrs. Then this reaction mixture was added slowly to the above reaction mixture for about 30min and stirred for 16h at room temperature. The reaction mixture was quenched with saturated ammonium acetate solution to pH-7. The resulting mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using 60-120 silica gel and 25% ethyl acetate in hexane as eluent to afford J-In-3.
  • 3
  • [ 619331-35-0 ]
  • (2-pyrazinyl)tributyltin [ No CAS ]
  • [ 676491-50-2 ]
YieldReaction ConditionsOperation in experiment
53% copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In DMF (N,N-dimethyl-formamide); at 90℃; for 4h; [0691] A mixture of <strong>[619331-35-0]7-bromo-4-methoxy-6-azaindole</strong> (1.160 g, 5.11 mmol) and 2-(tri-n-butylstannyl)pyrazine (2.07 g, 5.62 mmol) in 25 mL of dry DMF was degassed with a stream of Ar bubbles for 10 min. To this solution was added tetrakis(triphenylphosphine)palladium (0.590 g, 0.511 mmol) and CuI (0.097 g, 0.511 mmol) and the mixture was heated in a sealed tube at 90 C. for 4 h. The cooled mixture was filtered through methanesulfonic acid SCX cartridges (7×3 g) with MeOH, to remove triphenylphosphine oxide. The filtrate was evaporated and the residue triturated with MeOH to give the title compound (0.612 g, 53%) as a light yellow solid: [0692] 1Hnmr (400 MHz, DMSO-d6) δ 11.79 (br s, 1H), 9.63 (d, J=1.5 Hz, 1H), 8.75 (m, 1H), 8.64 (d, J=2.6 Hz, 1H), 8.04 (s, 1H), 7.56 (dd, J=3.0, 2.6 Hz, 1H), 6.64 (dd, J=3.0, 2.0 Hz, 1H), 4.08 (s, 3H). [0693] LCMS: m/e 227 (M+H)+.
  • 4
  • [ 110-89-4 ]
  • [ 619331-35-0 ]
  • [ 5518-52-5 ]
  • [ 2028-63-9 ]
  • [ 761446-35-9 ]
YieldReaction ConditionsOperation in experiment
95% With CuI;PdCl2(PhCN)2; Preparation of 4-Methoxy-7-(3-hydroxy-1-butyn-1-yl)-6-azaindole: To a mixture of 4-methoxy-7-bromo-6-azaindole (0.200 g, 0.88 mmol), PdCl2(PhCN)2 (0.017 g, 0.044 mmol), tri-2-furylphosphine (0.0410 g, 0.176 mmol) and CuI (0.017 g, 0.088 mmol) was added piperidine (10 mL), followed by 3-butyn-2-ol (0.09 mL, 1.15 mmol). The mixture was heated at 80 C. for 6 h and then the solvent was removed in vacuo. The residue was partitioned with EtOAc-H2O and then the aqueous phase was separated and re-extracted with EtOAc (*2). The combined organic layers were washed (H2O, brine), dried (Na2SO4) and concentrated to afford the title compound (0.200 g, 95%) as a brown solid which was of sufficient purity for use in the following step: 1H-NMR (MeOD): δ 7.60 (s, 1H), 7.35 (d, J=3.2 Hz, 1H) 6.55 (d, J=3.2 Hz, 1H), 4.72 (q, J=6.6 Hz, 1H), 3.94 (s, 3H), 1.48 (d, J=6.6 Hz, 3H).
  • 5
  • [ 619331-35-0 ]
  • Ar [ No CAS ]
  • (2-pyrazinyl)tributyltin [ No CAS ]
  • [ 676491-50-2 ]
YieldReaction ConditionsOperation in experiment
53% With CuI;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; Preparation of 4-Methoxy-7-pyrazinyl-6-azaindole: A mixture of <strong>[619331-35-0]7-bromo-4-methoxy-6-azaindole</strong> (1.160 g, 5.11 mmol) and 2-(tri-n-butylstannyl)pyrazine (2.07 g, 5.62 mmol) in 25 mL of dry DMF was degassed with a stream of Ar bubbles for 10 min. To this solution was added tetrakis(triphenylphosphine)palladium (0.590 g, 0.511 mmol) and CuI (0.097 g, 0.511 mmol) and the mixture was heated in a sealed tube at 90 C. for 4 h. The cooled mixture was filtered through methanesulfonic acid SCX cartridges (7*3 g) with MeOH, to remove triphenylphosphine oxide. The filtrate was evaporated and the residue triturated with MeOH to give the title compound (0.612 g, 53%) as a light yellow solid: 1Hnmr (400 MHz, DMSO-d6) δ 11.79 (br s, 1H), 9.63 (d, J=1.5 Hz, 1H), 8.75 (m, 1H), 8.64 (d, J=2.6 Hz, 1H), 8.04 (s, 1H), 7.56 (dd, J=3.0, 2.6 Hz, 1H), 6.64 (dd, J=3.0, 2.0 Hz, 1H), 4.08 (s, 3H). LCMS: m/e 227 (M+H)+.
  • 6
  • [ 1379269-07-4 ]
  • [ 619331-35-0 ]
YieldReaction ConditionsOperation in experiment
With phosphorus(V) oxybromide; In methoxybenzene; at 120℃; EXAMPLE J; Preparation of Compounds J of Formula 1 Process for the Preparation of Compound J-In-2 from J-In-I: <n="90"/>[00148] To a stirred solution of 4, 7-dimethoxy azaindole (1 eq.) in anisole was added phosphorus oxybromide (1 eq.) portion wise and the reaction mixture was slowly heated to 120 0C. Reaction mixture was allowed to stir at 120 0C for about 18h. Then, the reaction mixture was cooled to 10 0C and slowly quenched with ice- water mixture. The resulting mixture was neutralized with saturated sodium bicarbonate solution and then extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using 60-120 silica gel and 15% ethyl acetate in hexane as eluent to afford J-In-2.
  • 7
  • [ 619331-35-0 ]
  • [ 13057-17-5 ]
  • 7-bromo-4-methoxy-1-(methoxymethyl)-1H-pyrrolo[2,3-c]pyridine [ No CAS ]
 

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Technical Information

Categories

Related Functional Groups of
[ 619331-35-0 ]

Bromides

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Related Parent Nucleus of
[ 619331-35-0 ]

Pyridines

Chemical Structure| 1039046-54-2

A186292 [1039046-54-2]

4-((6-Bromopyridin-3-yl)oxy)-7-methoxyquinoline

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