Alternatived Products of [ 100382-00-1 ]
Alternatived Products of [ 100382-00-1 ]
Product Details of [ 100382-00-1 ]
| CAS No. : | 100382-00-1 |
MDL No. : | MFCD17252689 |
| Formula : |
C13H10N2O
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | N/A |
| M.W : | 210.23 g/mol |
Pubchem ID : | - |
| Synonyms : |
|
Safety of [ 100382-00-1 ]
Application In Synthesis of [ 100382-00-1 ]
- Downstream synthetic route of [ 100382-00-1 ]
- 1
-
[ 100382-00-1 ]
-
[ 100-58-3 ]
-
[ 1078734-11-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 77% |
In tetrahydrofuran at -30 - 20℃; for 5h; |
|
- 2
-
[ 2683-66-1 ]
-
[ 7677-24-9 ]
-
[ 100382-00-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 86.8% |
With N,N-Dimethylcarbamoyl chloride In dichloromethane at 0 - 20℃; |
2 Step 2: 4-(benzyloxy)picolinonitrile
To a solution of 4-(benzyloxy)pyridine 1-oxide (2.68 g, 13.3 mmol) in dichloromethane (15 mL) was added trimethylsilyl cyanide (2.0 mL, 15.7 mmol), followed by drop-wise addition of a solution of dimethylcarbamic chloride (1.5 mL, 15,733 mmol) indichloromethane (5 mL) at 0°C. The reaction was stirred at room temperature overnight. Aqueous sodium bicarbonate solution (15 mL, 10% wt) was added, and the mixture was stirred for 20 mm. The resulting mixture was extracted with dichloromethane, and the combined organic layers was washed with brine, dried over Na2504 and concentrated under reduced pressure to give 4-(benzyloxy)picolinonitrile (2.43 g, 86.8% yield) as a white solid. LC-MS(ESI) found: 211 [M+Hj |
| 84% |
With N,N-diethylcarbamoyl chloride In dichloromethane at 5 - 20℃; for 12h; |
|
- 3
-
[ 100382-00-1 ]
-
[ 100-58-3 ]
-
[ 1078734-06-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
Stage #1: 4-(benzyloxy)picolinonitrile; phenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 12h; |
General Procedures for Synthesis of 9a-d
General procedure: To a THF solution of 4-(benzyloxy)picolinonitrile 8 (1.0 eq) was added ArMgBr (1.0 M in Et2O, 1.0 eq) at -78 °C. After stirring for 1 h, the reaction mixture was quenched with 6 N HCl, and stirred for 12 h. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/hexanes) to afford the ketone 9. |
- 4
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[ 100382-00-1 ]
-
[ 352-13-6 ]
-
[ 1649982-96-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 4-(benzyloxy)picolinonitrile; 4-flourophenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 12h; |
General Procedures for Synthesis of 9a-d
General procedure: To a THF solution of 4-(benzyloxy)picolinonitrile 8 (1.0 eq) was added ArMgBr (1.0 M in Et2O, 1.0 eq) at -78 °C. After stirring for 1 h, the reaction mixture was quenched with 6 N HCl, and stirred for 12 h. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/hexanes) to afford the ketone 9. |
- 5
-
[ 100382-00-1 ]
-
[ 873-77-8 ]
-
[ 1649982-97-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 4-(benzyloxy)picolinonitrile; (4-chlorphenyl)magnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 12h; |
General Procedures for Synthesis of 9a-d
General procedure: To a THF solution of 4-(benzyloxy)picolinonitrile 8 (1.0 eq) was added ArMgBr (1.0 M in Et2O, 1.0 eq) at -78 °C. After stirring for 1 h, the reaction mixture was quenched with 6 N HCl, and stirred for 12 h. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/hexanes) to afford the ketone 9. |
- 6
-
[ 100382-00-1 ]
-
[ 4294-57-9 ]
-
[ 1649982-98-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 4-(benzyloxy)picolinonitrile; para-methylphenylmagnesium bromide In tetrahydrofuran; diethyl ether at -78℃; for 1h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether for 12h; |
General Procedures for Synthesis of 9a-d
General procedure: To a THF solution of 4-(benzyloxy)picolinonitrile 8 (1.0 eq) was added ArMgBr (1.0 M in Et2O, 1.0 eq) at -78 °C. After stirring for 1 h, the reaction mixture was quenched with 6 N HCl, and stirred for 12 h. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/hexanes) to afford the ketone 9. |
- 7
-
[ 100382-00-1 ]
-
[ 1649982-91-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C |
|
- 8
-
[ 100382-00-1 ]
-
[ 1649982-92-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C |
|
- 9
-
[ 100382-00-1 ]
-
[ 1649982-93-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C |
|
- 10
-
[ 100382-00-1 ]
-
[ 1649982-94-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C |
|
- 11
-
[ 100382-00-1 ]
-
[ 1649982-86-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h |
|
- 12
-
[ 100382-00-1 ]
-
[ 1649982-87-5 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h |
|
- 13
-
[ 100382-00-1 ]
-
[ 1649982-88-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h |
|
- 14
-
[ 100382-00-1 ]
-
[ 1649982-89-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 3 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h |
|
- 15
-
[ 100382-00-1 ]
-
[ 1649982-74-0 ]
-
[ 1649982-68-2 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 0 - 20 °C |
|
- 16
-
[ 100382-00-1 ]
-
[ 1649982-75-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 4 steps
1.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C
1.2: 12 h
2.1: sodium tetrahydroborate / methanol / 30 h / -78 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 1 h
4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 0 - 20 °C |
|
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