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[ CAS No. 1082674-24-5 ] {[proInfo.proName]}

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Chemical Structure| 1082674-24-5
Chemical Structure| 1082674-24-5
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Product Details of [ 1082674-24-5 ]

CAS No. :1082674-24-5 MDL No. :MFCD18633063
Formula : C10H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NOTGHQFEQASFGA-UHFFFAOYSA-N
M.W : 233.06 Pubchem ID :77174826
Synonyms :

Safety of [ 1082674-24-5 ]

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

Application In Synthesis of [ 1082674-24-5 ]

* 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.

  • Upstream synthesis route of [ 1082674-24-5 ]
  • Downstream synthetic route of [ 1082674-24-5 ]

[ 1082674-24-5 ] Synthesis Path-Upstream   1~4

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YieldReaction ConditionsOperation in experiment
25.4% With tris-(dibenzylideneacetone)dipalladium(0) In dimethyl sulfoxide; ethyl acetate; Petroleum ether Step 3.
Synthesis of 6-amino isoquinoline (#E3).
A solution of #A2 (4.0 g, 51.7 mmol), 6-bromoisoquinoline-1-carbonitrile #A3 (6.0 g, 25.9 mmol), BINAP (3.2 g, 5.2 mmol), Pd2(dba)3 (2.3 g, 2.6 mmol) and potassium phosphate (11.0 g, 51.7 mmol) in anhydrous DMSO (35 mL) was heated at 80° C. for 2 h.
The complete disappearance of the 6-bromoisoquinoline-1-carbonitrile #A3 was observed on TLC.
The reaction mixture was cooled to room temperature, filtered through Celite™ pad and the filtrate was diluted with water (100 mL).
The mixture was extracted with EtOAc (100 mL*3).
The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material which was purified by silica gel (100-200 mesh) column chromatography using 40percent EtOAc in petroleum ether as an eluting system to give #E3 as yellow solid (1.5 g, 25.4percent). Rf: 0.4 (60percent EtOAc in petroleum ether).
LCMS m/z=227.9 (M+H); 1H NMR (400 MHz, d6-DMSO): δ 1.18 (d, J=6.8 Hz, 3H), 3.36-3.47 (m, 1H), 3.48-3.53 (m, 1H), 3.60-3.66 (m, 1H), 6.80-6.82 (m, 2H), 7.32 (dd, J=2.4 Hz, 8.8 Hz, 1H), 7.72 (d, J=5.6 Hz, 1H), 7.87 (d, J=9.6 Hz, 1H), 8.30 (d, J=5.6 Hz, 1H).
24.3% With tris-(dibenzylideneacetone)dipalladium(0) In dimethyl sulfoxide Step 3.
Synthesis of 6-amino isoquinoline (#F3).
A solution of #F2 (4.5 g, 51.7 mmol), 6-bromoisoquinoline-1-carbonitrile (6.0 g, 25.9 mmol), BINAP (3.2 g, 5.1 mmol), Pd2(dba)3 (2.3 g, 2.6 mmol) and potassium phosphate (11.0 g, 51.7 mmol) in anhydrous DMSO (35 mL) was heated at 80° C. for 2 h.
The complete disappearance of the 6-bromoisoquinoline-1-carbonitrile was observed on TLC.
The reaction mixture was cooled to room temperature, filtered through a Celite™ pad and the filtrate was diluted with water (100 mL).
The mixture was extracted with EtOAc (100 mL*3).
The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude material.
The product was purified by chromatography on silica gel (100-200 mesh) using 10percent MeOH in DCM as eluant to give racemic #F3 as yellow solid (1.5 g, 24.3percent). Rf: 0.4 (50percent EtOAc in petroleum ether).
Chiral HPLC: two enantiomers (61.0percent, 39.0percent).
LCMS m/z=240.1 (M+H).
H NMR (400 MHz, d6-DMSO): δ 2.19-2.27 (m, 1H), 2.36-2.45 (m, 1H), 3.67-3.84 (m, 3H), 4.02-4.07 (m, 1H), 4.33-4.39 (m, 1H), 5.09 (t, J=4.8 Hz, 1H), 6.83 (d, J=1.6 Hz, 1H), 7.33 (dd, J=8.8 Hz, J=2.0 Hz, 1H), 7.78 (d, J=6.4 Hz, 1H), 7.97 (d, J=8.8 Hz, 1H), 8.36 (d, J=5.6 Hz, 1H).
Reference: [1] Patent: US2014/155390, 2014, A1, . Location in patent: Page/Page column
[2] Patent: US2014/155390, 2014, A1, . Location in patent: Page/Page column
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YieldReaction ConditionsOperation in experiment
61% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 25℃; for 1.25 h; Trimethylsilyl cyanide (52.0 mL, 580.0 mmol) was added dropwise to the stirred solution of A2 (65.0 g, 290.0 mmol) and DBU (50.0 mL, 348.0 mmol) in THF (500 mL) at room temperature over a period of 15 minutes. The reaction mixture was stirred at room temperature for 1 h. Water was added to the reaction mixture, and the solution was extracted with DCM. The organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude product. The product was purified by column chromatography using silica gel (100 - 200 mesh) with 0 - 4percent EtOAc in petroleum ether as an eluent to give A3 as white solid. Yield: 41 g (61 percent). Rf: 0.6 (30percent EtOAc in petroleum ether). LCMS m/z = 233 (M + 1 ). 1H NMR (400 MHz, cf6-DMSO): δ 8.07 (dd, J = 1 1.2, 2.0 Hz, 1 H), 8.21 (m, 2H), 8.55 (br s, 1 H), 8.77 (d, J = 7.6 Hz, 1 H).
Reference: [1] Patent: WO2015/181676, 2015, A1, . Location in patent: Page/Page column 133
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Reference: [1] Patent: WO2015/181676, 2015, A1,
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Reference: [1] Patent: WO2015/181676, 2015, A1,
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