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Product Details of [ 39806-90-1 ]

CAS No. :39806-90-1 MDL No. :MFCD05663860
Formula : C4H5IN2 Boiling Point : -
Linear Structure Formula :C3H2N2(CH3)I InChI Key :RSDRDHPLXWMTRJ-UHFFFAOYSA-N
M.W : 208.00 Pubchem ID :2734773
Synonyms :

Calculated chemistry of [ 39806-90-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.21
TPSA : 17.82 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 1.02
Log Po/w (MLOGP) : 0.99
Log Po/w (SILICOS-IT) : 1.43
Consensus Log Po/w : 1.19

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.21
Solubility : 1.27 mg/ml ; 0.00613 mol/l
Class : Soluble
Log S (Ali) : -0.84
Solubility : 30.2 mg/ml ; 0.145 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.75
Solubility : 3.67 mg/ml ; 0.0177 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 39806-90-1 ]

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

Application In Synthesis of [ 39806-90-1 ]

* 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 [ 39806-90-1 ]
  • Downstream synthetic route of [ 39806-90-1 ]

[ 39806-90-1 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 3469-69-0 ]
  • [ 74-88-4 ]
  • [ 39806-90-1 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere
Stage #2: for 12 h;
Under an atmosphere of nitrogen a solution of 4-iodo-1H-pyrazole (1.58 g; 8.0 mmol) in anhyd. THF wasadded dropwise to a freshly prepared suspension of sodium hydride (0.21 g; 8.7 mmol). The reactionmixture was stirred for 3 h and then 1.0 mL of methyl iodide (2.24 g; 15.8 mmol) was added dropwise.The mixture was stirred for additional 12 h and quenched by adding approximately 50 mL of water. Thecrude product was extracted with Et2O and dried over sodium sulfate. After evaporation of the solvent theproduct was obtained as a yellowish solid. Yield: 1.64 g (98percent)
95% at 20℃; for 96 h; To a solution of 4-iodopyrazole (1.3 g, 6.8 mmol) in dioxane (10 mL) was added iodomethane (0.42 mL, 6.8 mmol) and the resulting mixture stirred at room temperature for 96 h.
The mixture was concentrated in vacuo and the residue mixed with methylene chloride and filtered.
The filtrate was concentrated in vacuo to provide 1.35 g (95percent) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 7.47 (s, 1H), 7.38 (s, 1H), 3.90 (s, 3H).
95.9%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; for 22 h; Inert atmosphere
To a solution of 4-iodo-1H-pyrazole (3.88 g, 20 mmol) in DMF (50 mL) was addedNaH (1.66 g, 55.33 mmol, 80percent dispersion in mineral oil) at 0°C under N2 atmosphere. Thereaction was stirred at 0°C for 10 min followed by the addition of CH3I (2.5 mL, 38.76 mmol)slowly. The mixture was stirred at rt for 22 h, then quenched with H20 (100 mL) and extractedwith EtOAc (200 mL). The organic phase was dried over anhydrous Na2S04 and concentrated invacuo to give the title compound as a pale yellow solid (3.99 g, 95.9percent). The title compound wascharacterized by LC-MS as shown below:LC-MS (ESI, pos. ion) m/z: 209 [M+Ht.
95.9%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; for 22 h;
Under the protection of nitrogen, the 4-iodo -1H-pyrazole (3.88g, 20mmol) dissolved in DMF (50 ml) in, cooling to 0 °C, adding NaH (1.66g, 55 . 33mmol, in 80percent dispersion in mineral oil), mixture in 0 °C stirring 10 minutes, to continue to slowly adding the CH 3 I (2.5 ml, 38 . 76mmol). Reaction solution stirring the mixture at room temperature for 22 hours later, water (100 ml) quenching, and using EtOAc (200 ml) extraction. Organic phase Na 2 SO 4 drying, concentrating under reduced pressure, to obtain the title compound as a buff solid (3.99g, 95.9percent).
85% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17 h; 1-Methyl-4-iodopyrazole (18)[00203] 4-lodopyrazole (1 ); (5.0g 25.7mmole) was dissolved in DMF (50ml_), potassium carbonate (4.26g 30.9mmole) was added and stirred (2 mins) before iodomethane (1 .76ml_, 4.01 g 28.3mmole) was added. The reaction was stirred rapidly at r.t. for 17 hrs. It was filtered through a Celite pad. The filtrate was evaporated to a small volume, about 10ml_, using a rotary evaporator with a high vac. pump and the water bath at 60°C. Water (120ml_) was added to the residue. The filtered solids on the Celite pad were washed with ethyl acetate (50ml) and these washings were used to extract the product from the aqueous. The aqueous was extracted with more ethyl acetate (2x50ml_). The combined organics were washed with water (3x30ml_) and with brine; dried and evaporated to give the title compound as a solid 4.56g, 85percent. 1 H-NMR (CDCI3, 500MHz): δ 3.93 (s, 3H) 7.42 (s, 1 H), 7.50 (s, 1 H).
85%
Stage #1: With potassium carbonate In N,N-dimethyl-formamide for 0.0333333 h;
Stage #2: at 20℃; for 17 h;
1-Methyl-4-iodopyrazole (18)
4-Iodopyrazole (1) (5.0 g 25.7 mmole) was dissolved in DMF (50 mL), potassium carbonate (4.26 g 30.9 mmole) was added and stirred (2 mins) before iodomethane (1.76 mL, 4.01 g 28.3 mmole) was added.
The reaction was stirred rapidly at r.t. for 17 hrs.
It was filtered through a Celite pad.
The filtrate was evaporated to a small volume, about 10 mL, using a rotary evaporator with a high vac.
pump and the water bath at 60° C. Water (120 mL) was added to the residue.
The filtered solids on the Celite pad were washed with ethyl acetate (50 ml) and these washings were used to extract the product from the aqueous.
The aqueous was extracted with more ethyl acetate (2*50 mL).
The combined organics were washed with water (3*30 mL) and with brine; dried and evaporated to give the title compound as a solid 4.56 g, 85percent. 1H-NMR (CDCl3, 500 MHz): δ 3.93 (s, 3H) 7.42 (s, 1H), 7.50 (s, 1H).
45%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃;
To a suspension of NaH (0.463 g, 15.47 mmol, 80percent NaH/mineral oil) in DMF (100 mL) was added 4-iodo-pyrazole (1.0 g, 5.16 mmol) at 0 °C under N2 atmosphere, the mixture was stirred at 0 °C for 30 minutes, then iodomethane (0.64 mL, 10.31 mmol, d = 2.28) was added. The resulted mixture was warmed to rt and stirred overnight, then quenched with brine (100 mL), and concentrated in vacuo. The residue was diluted with EtOAc (200 mL) and washed with water (100 mL). The separated organic phase was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 2/1) to give the title compound as a light yellowish solid (490 mg, 45percent). NMR (400 MHz, CDCb): δ 7.48 (s, 1H), 7.40 (s, 1H), 3.91 (s, 3H).
45%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
NaH (0.463 g, 15.47 mmol, 80percent NaH / mineral oil)Suspended in DMF (100 mL)Cooled to 0 ° C,Then under the protection of nitrogen,To the reaction solution was added 4-iodopyrazole (1.0 g, 5.16 mmol),After stirring at 0 ° C for 30 minutes,Further iodomethane (0.64 mL, 10.3 lmmo 1, d = 2.28) was added,Warmed to room temperature, stirred overnight,The reaction was then quenched by the addition of brine (100 mL)The residue was diluted with EtOAc (200 mL), washed with water (100 mL), separated and the organic phase was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE / EtOAc (v / v) = 2/1) The title compound was a light yellow solid (490 mg, 45percent)
15 g With potassium carbonate In acetone at 20℃; General procedure: Step 1:
1-methyl-4-iodopyrazole
1H-4-iodopyrazole (20 g), potassium carbonate (28.45 g) and acetone (120 mL) were added into a round bottomed flask (250 mL) and agitated for 10 min.
Then iodomethane (17.56 g) was added and the mixture was agitated at room temperature over night.
After that, the mixture was filtrated and concentrated, the residue was recrystallized from n-hexane to prodce 1-methyl-1H-4-iodopyrazole (15 g) as white acicular crystal.
1H-NMR (300Hz, CDCl3) δ: 7.48 (s, 1H), 7.40 (s, 1H), 3.92 (s, 3H).
2.1 g With potassium carbonate In acetonitrile for 12 h; Reflux 4-iodopyrazole (2g, 10.3mmol), potassium carbonate (2.14g),Methyl iodide (1.72 g) and 25 mL acetonitrile,The reaction was refluxed for 12 h. Spin dry under reduced pressure and add 50 mL of water.Extracted three times with 50 mL of ethyl acetate, and the organic layers were combined.The organic layer was dried over anhydrous Na 2 SO 4 and dried under reduced pressure.1-Methyl-4-iodopyrazole (2.1 g) was obtained.

Reference: [1] Heterocycles, 2018, vol. 96, # 7, p. 1203 - 1215
[2] Patent: US6797723, 2004, B1, . Location in patent: Page/Page column 97
[3] Patent: WO2014/22128, 2014, A1, . Location in patent: Paragraph 0186
[4] Patent: CN103539777, 2016, B, . Location in patent: Paragraph 0455;0456
[5] Patent: WO2012/123745, 2012, A1, . Location in patent: Page/Page column 70
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 24, p. 10045 - 10065
[7] Patent: US2013/345181, 2013, A1, . Location in patent: Paragraph 0637
[8] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6628 - 6639
[9] Patent: WO2014/193647, 2014, A2, . Location in patent: Paragraph 0276
[10] Patent: CN104119331, 2018, B, . Location in patent: Paragraph 0790; 0791; 0793; 0794
[11] Patent: EP2650293, 2013, A1, . Location in patent: Paragraph 0072; 0073; 0074
[12] Patent: CN108484609, 2018, A, . Location in patent: Paragraph 0155; 0158
[13] Patent: US2018/312523, 2018, A1, . Location in patent: Paragraph 1800; 1801
  • 2
  • [ 930-36-9 ]
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YieldReaction ConditionsOperation in experiment
60% With dihydrogen peroxide; iodine In water at 24℃; A mixture of 1-methyl-1H-pyrazole (7) (37 gm, 0.6090 moles), iodine (57.1 gm,0.225 moles), hydrogen peroxide (9.2 gm, 0.27 moles) and DI water (I 10 ml) were stirred for 24 hour at 20-30°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 5-10°C. The reaction mixture was quenched with 20percent aqueous sodium bisulfate (100 ml) and stirred for I hour at 5-10°C. The solid obtained was filtered,V washed with cold DI water (100 ml) and dried at 40-45°C to obtain the product, 4-iodo-1-methyl- 1H-pyrazole. VDrywt : 56gmYield : 1.51 w/w(60percent) V
60% With dihydrogen peroxide; iodine In water at 20 - 30℃; for 24 h; Step 1: 4-iodo- 1-methyl-I H-pyrazoleA mixture of 1-methyl-IH-pyrazole (7) (37 gm, 0.6090 moles), iodine (57.1 gm, 0.225 moles), hydrogen peroxide (9.2 gm, 0.27 moles) and DI water (110 ml) were stirred for24 hour at 20-30°C. Progress of the reaction was monitored by HPLC and TLC. The reaction mixture was cooled to 5-10°C. The reaction mixture was quenched with 20percent aqueous sodium bisulfite (100 ml) and stirred for 1 hour at 5-10°C. The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-45°C to yield the product, 4-iodo-l- methyl-I H-pyrazole.Drywt 56gmYield : 1.51 w/w(60percent)
60% With dihydrogen peroxide; iodine In water at 20 - 30℃; for 24 h; Step 1 : 4-iodo- l -methyl- lH-pyrazole A mixture of 1 -methy 1-1 H-pyrazole (7) (37 gm, 0.6090 moles), iodine (57. 1 gm, 0.225 moles), hydrogen peroxide (9.2 gm, 0.27 moles) and DI water ( 1 10 ml) were stirred for 24 hour at 20-30°C. Progress of the reaction was monitored by HPLC and TLC. The reaction mixture was cooled to 5- 10°C. The reaction mixture was quenched with 20percent aqueous sodium bisulfite ( 100 ml) and stirred for 1 hour at 5-10°C. The solid product obtained was filtered off, washed with cold DI water ( 100 ml) and dried at 40-45°C to yield the product, 4-iodo- l - methyl- 1 H-pyrazole. Dry wt : 56 gm Yield : 1.51 w/w (60percent)
60% With dihydrogen peroxide; iodine In water at 20 - 30℃; for 24 h; A mixture of 1-methyl-1H-pyrazole (7) (37 gm, 0.6090 moles), iodine (57.1 gm, 0.225 moles), hydrogen peroxide (9.2 gm, 0.27 moles) and DI water (110 ml) were stirred for 24 hour at 20-30° C.
Progress of the reaction was monitored by HPLC and TLC.
The reaction mixture was cooled to 5-10° C.
The reaction mixture was quenched with 20percent aqueous sodium bisulfite (100 ml) and stirred for 1 hour at 5-10° C.
The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-45° C. to yield the product, 4-iodo-1-methyl-1H-pyrazole.

Reference: [1] Heterocycles, 2007, vol. 71, # 9, p. 1967 - 1974
[2] Tetrahedron Letters, 2008, vol. 49, # 25, p. 4026 - 4028
[3] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1329 - 1337
[4] Russian Chemical Bulletin, 1996, vol. 45, # 11, p. 2581 - 2584
[5] Russian Chemical Bulletin, 2014, vol. 63, # 2, p. 360 - 367[6] Izv. Akad. Nauk, Ser. Khim., 2014, # 2, p. 360 - 367
[7] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[8] Patent: WO2014/2109, 2014, A1, . Location in patent: Page/Page column 132
[9] Patent: WO2014/2110, 2014, A1, . Location in patent: Page/Page column 143
[10] Patent: WO2014/2111, 2014, A1, . Location in patent: Page/Page column 43
[11] Patent: US2015/112063, 2015, A1, . Location in patent: Paragraph 0236
[12] Chemical Communications, 2009, # 42, p. 6433 - 6435
[13] Russian Chemical Bulletin, 2010, vol. 59, # 8, p. 1549 - 1555
[14] Russian Chemical Bulletin, 2013, vol. 62, # 4, p. 1044 - 1051[15] Izv. Akad. Nauk, Ser. Khim., 2013, vol. 62, # 4, p. 1043 - 1050,8
  • 3
  • [ 74-88-4 ]
  • [ 39806-90-1 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With sodium hydride In tetrahydrofuran; hexane at 20℃; for 4.16667 h;
Stage #2: at 20℃; for 2.66667 h;
Step b); Preparation of Compound 3; Sodium hydride (0.680 g of a 60percent dispersion in oil, 17.0 mmol) was washed with hexanes (2 mL) diluted with THF (12 mL) and treated with a solution of 2 (3.00 g, 15.5 mmol) in THF (3 mL) over a period of 10 min. After stirring for 4 h at room temperature, a solution of methyl iodide (4.39 g, 31.9 mmol) in THF (3 mL) was added dropwise over a period of 10 min and the mixture stirred at room temperature for 2.5 h. The mixture was diluted with ether (100 mL) then washed with water (50 mL), brine (50 mL), dried over magnesium sulfate, filtered and concentrated to afford 3 (2.95 g, 92percent) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 7.49 (s, 1H), 7.41 (s, 1H), 3.92 (s, 3H); ESI MS m/z 209 [C4H5IN2+H]+.
Reference: [1] Patent: US2007/4786, 2007, A1, . Location in patent: Page/Page column 14
  • 4
  • [ 3469-69-0 ]
  • [ 74-87-3 ]
  • [ 39806-90-1 ]
YieldReaction ConditionsOperation in experiment
80% at 30 - 45℃; 4-iodopyrazole (20 g) and ethanol (100 ml) were added and stirred uniformly. KOH (11.6 g) and KI (0.9 g) were added and the methyl chloride gas was introduced into the liquid surface, Control temperature 30_45 ° C, GC tracking reaction end, add water 100g, dichloromethane extraction (40gX3), Concentrated to no flow liquid, with n-heptane 6ml beating, suction filter white solid, dry, weighing 17.2g, GC purity 98percent, yield 80percent;
Reference: [1] Patent: CN103601749, 2016, B, . Location in patent: Paragraph 0029-0030
  • 5
  • [ 1007521-93-8 ]
  • [ 762-72-1 ]
  • [ 39806-90-1 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 40, p. 5464 - 5466
  • 6
  • [ 5952-92-1 ]
  • [ 39806-90-1 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536
  • 7
  • [ 5952-93-2 ]
  • [ 39806-90-1 ]
  • [ 34091-53-7 ]
  • [ 34091-52-6 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1980, vol. 29, # 5, p. 778 - 784[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980, # 5, p. 1071 - 1077
  • 8
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Reference: [1] Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 200 - 207
  • 9
  • [ 39806-90-1 ]
  • [ 3994-50-1 ]
YieldReaction ConditionsOperation in experiment
64% With nitric acid In tetrahydrofuran; water at 20℃; for 3.5 h; General procedure: To iodopyrazole (1 mmol) dissolved in THF (10 mL), Fuajasite (250 mg) was added. Nitric acid (d 1.52 g/cm3, 10 mL) was added slowly and the mixture was stirred at room temperature for required time. The catalyst was recovered by filtration and the filtrate was extracted repeatedly with dichloromethane. The solvent was removed under vacuum to obtain nitropyrazole.
Reference: [1] Synthetic Communications, 2012, vol. 42, # 23, p. 3463 - 3471
[2] Russian Chemical Bulletin, 1996, vol. 45, # 11, p. 2581 - 2584
[3] Catalysis Communications, 2013, vol. 42, p. 35 - 39
  • 10
  • [ 39806-90-1 ]
  • [ 66121-71-9 ]
YieldReaction ConditionsOperation in experiment
63% With palladium diacetate; sodium carbonate In N,N-dimethyl acetamide at 100 - 110℃; for 12 h; Inert atmosphere To a solution of 4-iodo-1-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml), potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles)and sodium carbonate (27.98 gm, 0.264 moles) wereadded. The reaction mixture was evacuated and backfihled with nitrogen (3 times). The mixture was stirred for 12 hour at 100-1 10°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30°C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30°C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted withethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70°C. The mixture was degassed for 2 hour at reduced pressure at 60-70°C, cooled the mixture to 20-30°C: Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30°C. The solid product obtained was filtered, washedwith cold Dl water (100 ml) and dried at 40-50°C to afford the product, I-Methyl-IHpyrazole-4-carbonitrile.Drywt : 17.94gmYield : 0.32 w/w (63percent);
Reference: [1] Patent: WO2014/2109, 2014, A1, . Location in patent: Page/Page column 133
  • 11
  • [ 39806-90-1 ]
  • [ 66121-71-9 ]
YieldReaction ConditionsOperation in experiment
63% With palladium diacetate; sodium carbonate In N,N-dimethyl acetamide at 90 - 110℃; for 12 h; Inert atmosphere Step 2: l -methyl-l H-pyrazole-4-carbonitrile To a solution of 4-iodo- l -methyl- 1 H-pyrazole (55 gm, 0.264 moles) in N,N- dimethylacetamide ( 100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles) and sodium carbonate (27.98 gm, 0.264 ,moles). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90- 1 10°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30°C, to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 °C. The reaction mixture was filtered through pad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70°C. The mixture was degassed for 2 hour at reduced pressure at 60- 70°C, cooled the mixture to 20-30°C. Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30°C. The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-50 °C to yield the product, 1 -methyl- l H-pyrazole-4-carbonitrile,. Dry wt : 17.94 gm Yield : 0.32 w/w (63percent);
Reference: [1] Patent: WO2014/2111, 2014, A1, . Location in patent: Page/Page column 43; 44
  • 12
  • [ 39806-90-1 ]
  • [ 66121-71-9 ]
YieldReaction ConditionsOperation in experiment
63% With palladium diacetate; sodium carbonate In N,N-dimethyl acetamide at 90 - 110℃; for 12 h; Inert atmosphere Step 2: I-methyl-IH-pyrazole-4-carbonitrileTo a solution of 4-iodo-I-methyl-IH-pyrazole (55 gm, 0.264 moles) in N,Ndimethylacetamide (100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles),palladium (II) acetate (0.592 gm, 0,0026 moles) and sodium carbonate (27.98 gm, 0.264 moles). The reaction mixture was evacuated and backfilled with nitrogen (3 times). The mixture was stirred for 12 hour at 90-1 10°C. Progress of the reaction was monitored by HPLC. The reaction mixture was cooled to 20-30°C, to this added Dl water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30 °C. The reaction mixture was filtered throughpad of celite. The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 mm and separated the final aqueous layer and organic layer. The organic layer was washed with brine solution (200 ml). Ethyl acetate was recovered at reduced pressure at 60-70°C. The mixture was degassed for 2 hour at reduced pressure at 60- 70°C, cooled the mixture to 20-30°C. Hexane (400 ml) was added to the mixture and stirredfor 1 hour at 20-30°C. The solid product obtained was filtered off, washed with cold Dl water (100 ml) and dried at 40-50°C to yield the product, 1-methyl-IH-pyrazole-4-carbonitrile,.• Drywt 17.94gmYield 0.32 w/w (63percent);
Reference: [1] Patent: WO2014/2110, 2014, A1, . Location in patent: Page/Page column 143
  • 13
  • [ 39806-90-1 ]
  • [ 66121-71-9 ]
YieldReaction ConditionsOperation in experiment
63% With palladium diacetate; sodium carbonate In N,N-dimethyl acetamide at 90 - 110℃; for 12 h; Inert atmosphere To a solution of 4-iodo-1-methyl-1H-pyrazole (55 gm, 0.264 moles) in N,N-dimethylacetamide (100 ml) was added potassium ferrocyanide (24.5 gm, 0.058 moles), palladium (II) acetate (0.592 gm, 0.0026 moles) and sodium carbonate (27.98 gm, 0.264 moles).
The reaction mixture was evacuated and backfilled with nitrogen (3 times).
The mixture was stirred for 12 hour at 90-110° C.
Progress of the reaction was monitored by HPLC.
The reaction mixture was cooled to 20-30° C., to this added DI water (500 ml), ethyl acetate (500 ml) and stirred for 1 hour at 20-30° C.
The reaction mixture was filtered through pad of celite.
The organic layer was separated and aqueous layer was extracted with ethyl acetate (200 ml), stirred for 15 min and separated the final aqueous layer and organic layer.
The organic layer was washed with brine solution (200 ml).
Ethyl acetate was recovered at reduced pressure at 60-70° C.
The mixture was degassed for 2 hour at reduced pressure at 60-70° C., cooled the mixture to 20-30° C. Hexane (400 ml) was added to the mixture and stirred for 1 hour at 20-30° C.
The solid product obtained was filtered off, washed with cold DI water (100 ml) and dried at 40-50° C. to yield the product, 1-methyl-1H-pyrazole-4-carbonitrile.
Reference: [1] Patent: US2015/112063, 2015, A1, . Location in patent: Paragraph 0237
  • 14
  • [ 39806-90-1 ]
  • [ 78191-00-1 ]
  • [ 37687-18-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3644 - 3649
  • 15
  • [ 39806-90-1 ]
  • [ 111-34-2 ]
  • [ 37687-18-6 ]
YieldReaction ConditionsOperation in experiment
2.4 g With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; sodium carbonate In butan-1-ol for 4 h; Inert atmosphere; Reflux General procedure: Step 2:
1-[(1-methyl)-4-pyrazolyl]ethanone
1-methyl-4-iodopyrazole (10 g), vinyl-n-butyl ether (24 g), palladium acetate (396 mg), 1,3-bi(diphenyl phosphine)propane (988 mg), sodium carbonate (12.7 g) and n-butylalcohol (100 mL) were added in a round bottomed flask (250 mL).
The mixture was refluxed under an argon atmosphere for 4 h, cooled to room temperature, filtrated and treated under reduced pressure to remove solvent thereof.
The residue was purified by column chromatography (dichloromethane: methanol=50: 1) to get 1-[(1-methyl)-4-pyrazolyl]ethanone (2.4 g) as yellowish solid.
1H-NMR (300Hz, CDCl3) δ: 7.88 (s, 1H), 7.85 (s, 1H), 3.93 (s, 3H), 2,42 (s, 3H).
Reference: [1] Patent: EP2650293, 2013, A1, . Location in patent: Paragraph 0075; 0076
  • 16
  • [ 39806-90-1 ]
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 5952-93-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 6903 - 6908
[2] European Journal of Organic Chemistry, 2014, vol. 2014, # 29, p. 6418 - 6430
  • 17
  • [ 39806-90-1 ]
  • [ 288148-34-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6628 - 6639
  • 18
  • [ 39806-90-1 ]
  • [ 61676-62-8 ]
  • [ 761446-44-0 ]
YieldReaction ConditionsOperation in experiment
1 g
Stage #1: With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 0℃; for 1 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 1.5 h;
To 1-methyl-4-iodopyrazole (1.0 g) and 10 mL of THF,Under the protection of nitrogen, slowly add isopropylmagnesium chloride/lithium chloride solution (3.97mL), the temperature during the dropwise addition does not exceed 0 °C,After the addition, stir for 1 h, then at 0 ° C,Slowly add isopropyl pinacol borate (1.11g) to control the temperature not to exceed 0 ° C, and then stir at room temperature for 1.5 h after the addition.After the reaction was completed, 10 mL of a saturated ammonium chloride solution was added dropwise.Quenched.Then add 50 mL of ethyl acetate and 10 mL of saturated ammonium chloride solution.The organic layer was separated, and the aqueous layer was extracted twice with 50 mL of ethyl acetate. The organic layer was combined and dried over anhydrous Na2SO?Dry under reduced pressure,The title product (1 g) was obtained.
Reference: [1] Patent: CN108484609, 2018, A, . Location in patent: Paragraph 0155; 0156; 0157; 0159
  • 19
  • [ 39806-90-1 ]
  • [ 5467-74-3 ]
  • [ 1191616-45-1 ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,2-dimethoxyethane; water at 90℃; for 0.116667 h; Microwave irradiation; Inert atmosphere General procedure: 4-Iodo-1-methyl-1H-pyrazole 1 (101 mg, 0.5 mmol) and phenylboronic 2 (59 mg, 0.5 mmol) were dissolved in DME (3 mL) and H2O (1.2 mL) in a microwave vial under a nitrogen atmosphere. Pd(PPh3)4 (2 mmolpercent, 11.6 mg) and Cs2CO3 (407.3 mg, 1.25 mmol) were added, and the reaction mixture was irradiated in a microwave apparatus at 90 °C for 5–12 min. After the reaction mixture was cooled to ambient temperature, the product was concentrated, and the crude mixture was purified by silica gel column chromatography using petroleum ether/acetone as eluent to give the title compound.
Reference: [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 705 - 709
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