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CAS No. : | 1659-31-0 | MDL No. : | MFCD00191407 |
Formula : | C11H8N2O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GCSAXWHQFYOIFE-UHFFFAOYSA-N |
M.W : | 216.19 | Pubchem ID : | 2757370 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 triethylamine; In dichloromethane; at 20℃; for 15h;Inert atmosphere; | Under nitrogen atmosphere, to a stirred mixture of 3-phenylphenyl methanol (0.3 g, 1.63 mmol) in dry CH2C12 (3 mL), Et3N (0.340 mL, 2.44 mmol) and di-2-pyridyl carbonate (0.387 g, 1.79 mmol) were added. The reaction mixture was left at rt for 15h, diluted with CH2C12 and washed first with a saturated NH4C1 solution (3 mL) and subsequently with a saturated NaHC03 solution (3x3 mL). The organic fraction was dried over Na2S04, filtered and concentrated to dryness to afford a dark oil (0.487 g, 98%), as a mixture (ratio 1:3) of 3- phenylphenyl)methyl-2-pyridyl-carbonate and 3-phenylphenyl)methyl-2-oxopyridine 1- carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z: 328 [M-Na]+, 306 [M-H]+, 262, 167. | |
With dmap; In dichloromethane; at 20℃; for 16h;Inert atmosphere; | Under nitrogen atmosphere, to a stirred mixture of commercially available (3- phenylphenyl)-methanol (0.30 g, 1.82 mmol) in dry CH2C12 (8.0 mL), DMAP (0.022 g, 0.18 mmol) and 2-DPC (0.47 1 g, 2.18 mmol) were added. The reaction mixture was left at r.t. for 16 h, then diluted with CH2C12 (50 mL) and sequentially washed with sat. NH4C1 solution (50 mL),sat. NaHCO3 solution (3 x 50 mL) and brine (50 mL). The organic layer was dried over Na2504, filtered and concentrated to dryness to afford an oily product (0.426 g), as a mixture (1:1.7 ratio) of (3 -phenylphenyl)-methyl-2-pyridyl carbonate and (3 -phenylphenyl)-methyl-2-oxopyridine- 1- carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. R = 2.33 mm; MS (ESI) m/z: 306 [M-H], 228 [M-Na]. | |
With triethylamine; In dichloromethane; at 20℃; for 15h;Inert atmosphere; | Step 3. Preparation of (3-phenylphenyl)methyl-2-pyridyl-carbonate and 3-phenylphenyl)methyl-2-oxopyridine 1-carboxylate Under nitrogen atmosphere, to a stirred mixture of 3-phenylphenyl methanol (0.3 g, 1.63 mmol) in dry CH2Cl2 (3 mL), Et3N (0.340 mL, 2.44 mmol) and di-2-pyridyl carbonate (0.387 g, 1.79 mmol) were added. The reaction mixture was left at rt for 15 h, diluted with CH2Cl2 and washed first with a saturated NH4Cl solution (3 mL) and subsequently with a saturated NaHCO3 solution (3*3 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford a dark oil (0.487 g, 98%), as a mixture (ratio 1:3) of 3-phenylphenyl)methyl-2-pyridyl-carbonate and 3-phenylphenyl)methyl-2-oxopyridine 1-carboxylate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.045 g | Under nitrogen atmosphere, to a stirred mixture of (3S,4R)-2-methyl-4-oxo-3- oxetanylammonium toluene-4-sulfonate (0.120 g, 0.44 mmol) in dry CH2C12 (1 mL), DIPEA (0.072 mL, 0.44 mmol) was added dropwise. Subsequently, the crude mixture containing (3- phenylphenyl)-methyl-2-oxopyridine 1 -carboxylate (0.402 g, 1.32 mmol) dissolved in dry CH2C12 (2 mL) was added. The reaction mixture was stirred 15h at rt, concentrated to dryness and purified by column chromatography using a Teledyne ISCO apparatus, eluting with cyclohexane/TBME (from 100:0 to 70:30) to afford the title compound (0.045 g, 32%) as a white solid. MS (ESI) m/z: 334 [M-Na]+. 1H-NMR (DMSO-d6): delta 1.36 (d, J= 6.4, 3H), 4.88 (dq, Ji=J2= 6.3, 1H), 5.08-5.29 (m, 2H), 5.47 (dd, J= 9.3, J=6.2, 1H), 7.31-7.79 (m, 9H), 8.40 (d, J= 9.3, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Under nitrogen atmosphere, to a stirred mixture of <strong>[457889-46-2][4-[4-(trifluoromethyl)-phenyl]-phenyl]-methanol</strong> (0.3 g, 1.19 mmol) in dry CH2Cl2 (2.0 mL), DMAP (0.015 g, 0.12 mmol) and di-2-pyridyl-carbonate (0.309 g, 1.43 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2Cl2 and washed first with a saturated NH4Cl solution (3.0 mL) and subsequently with a saturated NaHCO3 solution (3×3 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford a colorless oil (0.3 g, 68%), as a mixture (ratio 1.8:1) of 2-pyridyl-[4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2-oxopyridine-1-carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. To a stirred mixture of D-threonine (0.063 g, 0.53 mmol) and NaHCO3 (0.067 g, 0.8 mmol) in H2O (3.0 mL), the crude mixture containing 2-pyridyl-[4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2-oxopyridine-1-carboxylate (0.3 g, 0.8 mmol) in THF (3.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et2O (3×5 mL). The aqueous phase was acidified with 2.0 M HCl solution to pH 2-3 and subsequently extracted with EtOAc (3×10 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford the title compound as transparent oil (0.21 g, quant.), which was used in the next step without further purification. MS (ESI) m/z: 415 [M-NH4]+; (ESI) m/z: 396 [M-H]-. 1H NMR (DMSO-d6): delta 1.11 (d, J=6.4 Hz, 3H), 3.97 (dd, J=3.5, 8.9 Hz, 1H), 4.05-4.12 (dq, J=3.5, 6.4 Hz, 1H), 5.13 (s, 2H), 7.00 (d, J=8.9 Hz, 1H), 7.51 (d, J=8.1 Hz, 2H), 7.75 (d, J=8.1 Hz, 2H), 7.82 (d, J=8.1 Hz, 2H), 7.91 (d, J=8.1 Hz, 2H), 12.59 (s, 1H). | |
0.21 g | To a stirred mixture of D-threonine (0.063 g, 0.53 mmol) and NaHC03 (0.067 g, 0.8 mmol) in H20 (3.0 mL), the crude mixture containing 2-pyridyl-[4-[4-(trifluoromethyl)- phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2- oxopyridine-l-carboxylate (0.3 g, 0.8 mmol) in THF (3.0 mL) was added. After 15 h at rt, the crude mixture was rotary evaporated to remove the organics and subsequently extracted with Et20 (3x5 mL). The aqueous phase was acidified with 2.0 M HC1 solution to pH 2-3 and subsequently extracted with EtOAc (3x10 mL). The organic fraction was dried over Na2S04, filtered and concentrated to dryness to afford the title compound as transparent oil (0.21 g, quant.), which was used in the next step without further purification. MS (ESI) m/z: 415 [M- NH4]+; (ESI) m/z: 396 [M-H]-. 1H NMR (DMSO-d6): delta 1.1 1 (d, J= 6.4 Hz, 3H), 3.97 (dd, J= 3.5, 8.9 Hz, 1H), 4.05 - 4.12 (dq, J= 3.5, 6.4 Hz, 1H), 5.13 (s, 2H), 7.00 (d, J= 8.9 Hz, 1H), 7.51 (d, J= 8.1 Hz, 2H), 7.75 (d, J= 8.1 Hz, 2H), 7.82 (d, J= 8.1 Hz, 2H), 7.91 (d, J= 8.1 Hz, 2H), 12.59 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; In dichloromethane; at 20℃; for 15h;Inert atmosphere; | Under nitrogen atmosphere, to a stirred mixture of [4-[4-(trifluoromethyl)-phenyl]- phenylj-methanol (0.3 g, 1.19 mmol) in dry CH2C12 (2.0 mL), DMAP (0.015 g, 0.12 mmol) and di-2-pyridyl-carbonate (0.309 g, 1.43 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2C1 and washed first with a saturated NH4CI solution (3.0 mL) and subsequently with a saturated NaHC03 solution (3X3 mL). The organic fraction was dried over Na2S0 , filtered and concentrated to dryness to afford a colorless oil (0.3 g, 68%), as a mixture (ratio 1.8: 1) of 2-pyridyl-[4-[4-(trifluoromethyl)- phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2- oxopyridine-l-carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z : 396 [M-Na]+, 412 [M-K]+. | |
With dmap; In dichloromethane; at 20℃; for 15h;Inert atmosphere; | Under nitrogen atmosphere, to a stirred mixture of <strong>[457889-46-2][4-[4-(trifluoromethyl)-phenyl]-phenyl]-methanol</strong> (0.3 g, 1.19 mmol) in dry CH2Cl2 (2.0 mL), DMAP (0.015 g, 0.12 mmol) and di-2-pyridyl-carbonate (0.309 g, 1.43 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2Cl2 and washed first with a saturated NH4Cl solution (3.0 mL) and subsequently with a saturated NaHCO3 solution (3×3 mL). The organic fraction was dried over Na2SO4, filtered and concentrated to dryness to afford a colorless oil (0.3 g, 68%), as a mixture (ratio 1.8:1) of 2-pyridyl-[4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl carbonate and [4-[4-(trifluoromethyl)-phenyl]-phenyl]-methyl-2-oxopyridine-1-carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z: 396 [M-Na]+, 412 [M-K]+. |