Structure of 64443-05-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 64443-05-6 |
Formula : | C8H12CuF6N4P |
M.W : | 372.72 |
SMILES Code : | [P+5]([F-])([F-])([F-])([F-])([F-])[F-].[Cu+](N#CC)(N#CC)(N#CC)N#CC |
MDL No. : | MFCD00064810 |
InChI Key : | GNQXUMGHBSAQBV-UHFFFAOYSA-N |
Pubchem ID : | 11068737 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
* 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 |
---|---|---|
69% | In dichloromethane; at 20℃; for 0.5h; | General procedure: [Cu(MeCN)4]PF6 (75 mg, 0.20mmol) was added to dppp (82 mg, 0.20mmol) in 5mL of dichloromethane. Then, bpy (32 mg, 0.20mmol) was added and the solution immediately changed to yellow. The reaction mixture was stirred for 30 min at room temperature. Diethyl ether was added to the solution to precipitate the product as a yellow solid, which was filtered and washed with diethyl ether: yield, 126 mg (0.162mmol, 81percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In dichloromethane; at 20℃; for 1.5h; | General procedure: [Cu-(MeCN)4]PF6 (74 mg, 0.20 mmol) was added to TolBINAP(135 mg, 0.20 mmol) in 2 mL CH2Cl2. Then, bpy (31 mg, 0.20mmol) was added. The yellow reaction mixture was stirred for90 minutes at room temperature. Diethyl ether (25 mL) wasadded to the solution to precipitate the product as a yellowsolid, which was filtered and dried in vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 0.5h;Inert atmosphere; | 1 (0.98mmol, 315mg) and 1,2-diacetonitrilebenzene (1.13mmol, 176mg) were dissolved in acetonitrile (25mL) and heated to reflux. DBU (1,8-Diazabicyclo [5.4.0] undec-7-ene, 1mmol, 156mg) was then added to the solution which turned dark green at once. After 4h of reflux, the medium was let to return to room temperature and water was added. The mixture was extracted twice with dichloromethane. The organic phase was then dried on sodium sulphate, filtered and evaporated to dryness. The crude was chromatographied on silica gel (eluent: dichloromethane/triethylamine 98/2 (v/v)). The first fraction contained the desired compound and 1,2-diacetonitrilebenzene (respectively 43% and 57% molar, estimated by NMR). The latter mixture was dissolved in dichloromethane, degassed by argon bubbling, and a degassed solution of Cu(CH3CN)4PF6 (0.21mmol, 77mg) was syringed herein. After 30min, the deep red solution is evaporated to dryness and subjected to chromatography column on silica gel (eluent: gradient from pure dichloromethane to a mixture of dichloromethane and methanol (98/2 v/v)). The collected orange fraction was then dissolved in acetonitrile (5mL) and a saturated aqueous solution of KCN (5mL) was added. The solution changes from dark red to light yellow within a few seconds. The latter was extracted twice with dichloromethane, dried on sodium sulphate, filtered and evaporated to dryness. The resulting yellow powder was the desired compound. Yield: 189mg (44% on the overall process). 1H NMR (300MHz, CDCl3, 25C): delta=9.69 (2H, d, J=8.7Hz), 8.63 (2H, dd, J=3.3Hz, J=6.6Hz), 7.92, (2H, dd, J=3.3Hz, J=6.6Hz), 7.60 (2H, d, J=8.7Hz), 3.21 (4H, m), 1.94 (4H, m), 1.53 (4H, m), 1.03 (6H, t, 7.5Hz) ppm. |