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Chemical Structure| 411235-57-9
Chemical Structure| 411235-57-9
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Product Details of [ 411235-57-9 ]

CAS No. :411235-57-9 MDL No. :MFCD04038750
Formula : C3H7BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WLVKDFJTYKELLQ-UHFFFAOYSA-N
M.W : 85.90 Pubchem ID :2760897
Synonyms :

Calculated chemistry of [ 411235-57-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 23.56
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.09
Log Po/w (WLOGP) : -0.44
Log Po/w (MLOGP) : -1.03
Log Po/w (SILICOS-IT) : -1.32
Consensus Log Po/w : -0.58

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.25
Solubility : 48.3 mg/ml ; 0.563 mol/l
Class : Very soluble
Log S (Ali) : -0.31
Solubility : 42.3 mg/ml ; 0.493 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.74
Solubility : 468.0 mg/ml ; 5.45 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 411235-57-9 ]

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 [ 411235-57-9 ]

* 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 [ 411235-57-9 ]
  • Downstream synthetic route of [ 411235-57-9 ]

[ 411235-57-9 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 411235-57-9 ]
  • [ 16545-68-9 ]
YieldReaction ConditionsOperation in experiment
60% With dihydrogen peroxide; sodium hydroxide In water at 5℃; for 1 h; Step 1: cyclopropanol (0104) (0105) Cyclopropylboronic acid (10g, 0.116mol), sodium hydroxide aqueous solution (8.37g, 0.209mol, added to 100ml water) were added into a 1L reaction flask, and hydrogen peroxide (34percent, 80mL) was slowly dropped thereinto under ice bath and the temperature was kept not higher than 5°Cduring the process of dropping. After adding, the mixture was stirred at 5°C for 1 hour. After completion of the reaction, a saturated sodium thiosulfate aqueous solution was slowly dropped to terminate the reaction until the potassium iodide-starch test paper does not change color. The reaction solution was extracted with diethyl ether for three times and the combined organic phase was washed with saturated brine, dried, filtered and concentrated at 0°C to obtain the title compound (colorless oil, 4g, 60percent), which may be used directly for the subsequent reaction. (MS: [M+1] none)
43% With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 1 h; A solution of aqueous hydrogen peroxide (30percent, 84 equiv) was added drop-wise to a stirring solution of cyclopropylboronic acid (1 equiv) in aqueous 10percent sodium hydroxide (1 equiv) at 0° C. The resulting mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with saturated aqueous sodium thiosulfate pentahydrate and extracted with diethyl ether. The combined organic were dried over sodium sulfate, filtered, and concentrated in vacuo at 0° C. to give cyclopropanol (43percent yield) as clear oil. 1H NMR (400 MHz, CHLOROFORM-d1) δ ppm 3.49-3.53 (m, 1H) 2.22 (br. s., 1H) 0.52-0.60 (m, 2H) 0.42-0.52 (m, 2H).
36.4% at 0℃; for 1.5 h; To a solution of cyclopropylboronic acid (0.65 g, 7.57 mmol) in 10percent NaOH (5.0mL) at 0 °C was added a solution of 30percent hydrogen peroxide (21.44 mL, 189 mmol)dropwise. The reaction mixture was stirred at 0 °C for 1.5 h. The reaction mixture was diluted with diethyl ether, quenched with saturated NaHSO3 (15 mL) at 0 °C. After stirring for 15 mm, the organic layer was collected, washed with brine, dried over sodium sulfate and concentrated at 0 °C to give Intermediate 33A (0.16 g, 2.75 mmol, 36.4 percentyield) as colorless liquid. It was used for the next step without further purification. ‘H NMR (400MHz, chloroform-d) ö 3.62-3.41 (m, 1H), 0.69-0.40 (m, 4H).
33% With dihydrogen peroxide; sodium hydroxide In water at 0℃; for 1 h; A solution of aqueous H2O2 (30percent, 20 mL, 200 mmol) was added dropwise with continuous stirring at 0° C. to a suspension of cyclopropyl boronic acid (0.62 g, 7.2 mmol) in 10percent aqueous NaOH (5 mL). The resulting mixture was stirred for 1 hour at 0° C. The reaction mixture was quenched with saturated aqueous Na2S2O3 and extracted with Et2O. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo at 0° C. The material was dissolved in Et2O (15 ml), 4 Molecular sieves were added and it was left overnight at room temperature to yield the title compound as pale yellow oil (140 mg, 33percent):1H NMR (400 MHz, CDCl3): δ 0.43 (m, 4H), 3.36 (m, 1H).

Reference: [1] Patent: EP3150592, 2017, A1, . Location in patent: Paragraph 0103; 0104; 0105
[2] Patent: US2014/200206, 2014, A1, . Location in patent: Paragraph 0319
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 21, p. 8989 - 9002
[4] Patent: WO2018/13774, 2018, A1, . Location in patent: Page/Page column 356
[5] Patent: US2012/10183, 2012, A1, . Location in patent: Page/Page column 54
[6] Patent: TW2016/2093, 2016, A, . Location in patent: Paragraph 0322
[7] Patent: WO2017/7701, 2017, A1, . Location in patent: Page/Page column 36-37
[8] Patent: US2016/194302, 2016, A1, . Location in patent: Paragraph 0411; 0412
  • 2
  • [ 7732-18-5 ]
  • [ 411235-57-9 ]
  • [ 16545-68-9 ]
Reference: [1] Patent: WO2015/65937, 2015, A1, . Location in patent: Paragraph 000295
  • 3
  • [ 7722-84-1 ]
  • [ 411235-57-9 ]
  • [ 16545-68-9 ]
Reference: [1] Patent: US2015/166505, 2015, A1, . Location in patent: Paragraph 0328; 0329; 0330
  • 4
  • [ 99-90-1 ]
  • [ 411235-57-9 ]
  • [ 6921-45-5 ]
YieldReaction ConditionsOperation in experiment
95% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 8 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
1.0 g With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; dimethyl sulfoxide at 100℃; for 48 h; To a solution of 1-(4-bromophenyl)ethanone (3.Og, 0.0150 mmol) in mixture of DMSO: water (3:1, 30 mL) was added tripotassium phosphate (9.5 g, 0.045 mmol), 1,1 ‘-bi s(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane (0.200 g,0.245 mmol) and cyclopropylboronic acid (1.9 g, 0.022 mmol). The reactionmixture was heated at 100 °C for 48 h. The reaction mass was quenched with water and extracted with EtOAc. The organic layer were washed with water and brine, dried over Na2504 and concentrated. The obtained solid was purified by column chromatography on silica gel to afford 1.0 g of the title product. ‘H NIVIR (300 IVIFIz, DMSO d6): 7.86-7.83 (d, J = 7.8 Hz, 2H), 7.13.7.10 (d, J = 7.8 Hz, 2H), 2.57 (s,3H), 1.94 (m, 1H), 1.07-1.05 (q, J= 7.2 Hz, 2H),0.79-0.77 (d, J= 4.8 Hz, 2H).
Reference: [1] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
[2] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[3] Patent: WO2015/59618, 2015, A1, . Location in patent: Page/Page column 42
[4] Journal of the American Chemical Society, 2016, vol. 138, # 20, p. 6598 - 6609
[5] Patent: WO2016/201168, 2016, A1, . Location in patent: Paragraph 0662
  • 5
  • [ 99-91-2 ]
  • [ 411235-57-9 ]
  • [ 6921-45-5 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
  • 6
  • [ 1122-91-4 ]
  • [ 411235-57-9 ]
  • [ 20034-50-8 ]
YieldReaction ConditionsOperation in experiment
93.2% With potassium phosphate tribasic trihydrate; palladium diacetate; tricyclohexylphosphine In water; toluene at 80℃; for 15 h; Inert atmosphere [0188] To a mixture of 4-bromobenzaldehyde (13.5 g,0.0734 mol), cyclopropylboronic acid (6.3 g, 0.0734 mol),K3P04 .3H20 (33.3 g, 0.147 mol) and PCy3 (20.5 g, 0.0734mol) in toluene/H20 (180 mL, 5:1) was added Pd(OAc )2 (500mg) under N2 . The reaction was heated at 80° C. for 15 hrsunder N2 . The reaction was complete detected by LCMS.Toluene and H20 were removed by vacuum. The crude productwas purified by colunm chromatography on silica gel(eluted with PE:Et0Ac=20: 1) to give the title compound (5.0g, yield: 93.2percent) as a yellow oil. 1 H-NMR ( 400 MHz, CDC13 )oppm 9.94 (s, lH), 7.76 (d, 2H, 1=7.6 Hz), 7.18 (d, 2H, 1=7.6Hz), 2.00-1.94 (m, lH), 1.11-1.07 (m, 2H), 0.82-0.80 (m,2H).
80% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In water; toluene at 110℃; for 16 h; Inert atmosphere; Microwave irradiation 4-Cyclopropylbenzaldehyde was prepared in 80percent yield according to the Example 8, Step A substituting cyclohex-l-en-l-ylboronic acid for cyclopropylboronic acid and 6-(4-bromophenyl)-3-((2-chlorophenyl)thio)-6-(thiophen-3-yl) piperidine -2,4-dione for 4-bromobenzaldehyde
61% With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 20 - 100℃; Inert atmosphere [0721] Synthesis of 4-cyclopropylbe yde: [0722] To a stirred solution of 4-bromobenzaldehyde (500 mg, 2.70 mmol) in toluene (20 mL) under argon atmosphere were added cyclopropyl boronic acid (300 mg, 3.51 mmol), potassium phosphate (1.72 g, 8.10 mmol) and tricyclohexyl phosphine (38 mg, 0.13 mmol) at RT and purged under argon for 30 min. Then palladium acetate (30 mg, 0.13 mmol) was added to the reaction mass; heated to 100 °C and stirred for 8 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was diluted with ice cold water (25 mL) and extracted with EtOAc (2 x 30 mL). The combined organic extracts were washed with saturated NaHC03 solution (15 mL), dried over sodium sulfate, filtered and concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 10percent EtOAc/ Hexanes to afford 4- cyclopropylbenzaldehyde (240 mg, 61percent) as pale yellow liquid. [0723] 1H-NMR (CDC13, 400 MHz): δ 9.94 (s, 1H), 7.78 (d, 2H), 7.20 (d, 2H), 2.00-1.95 (m, 1H), 1.12-1.07 (m, 2H), 0.84-0.78 (m, 2H); TLC: 20percent EtOAc/ Hexanes (R 0.5).
1.70 g With potassium phosphate; triphenylphosphine In water; toluene at 100℃; for 18 h; To a solution of 4-bromobenzaldehyde (3.4 g, 0.0 180 mmol) in mixture of toluene:water (40 mL: 3.0 mL) was added tripotassium phosphate (9.5 g, 0.045 mmol), triphenylphosphine (0.719 g, 0.002 mmol) and cyclopropylboronic acid (2.3 g, 0.027 mmol). The reaction mixture was heated at 100°C for 18 h. The reaction mass wasquenched with water and extracted with EtOAc. The organic layer were washed with water and brine, dried over Na2504 and concentrated. The obtained solid was purified by column chromatography to afford 1.70 g of the title product. ‘H NMR (300 IVIHz, DMSO d6): 9.94 (s, 1H), 7.77-7.75 (d, J = 8.4 Hz, 2H), 7.20-7.17 (d, J = 7.8 Hz, 2H), 1.97 (m, 1H), 1.11-1.08 (m, 2H), 0.82-0.80 (m, 2H).

Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[2] Patent: US2016/31892, 2016, A1, . Location in patent: Paragraph 0187-0188
[3] Tetrahedron Letters, 2002, vol. 43, # 39, p. 6987 - 6990
[4] Patent: WO2015/140133, 2015, A1, . Location in patent: Page/Page column 137
[5] Patent: WO2013/142269, 2013, A1, . Location in patent: Paragraph 0721; 0722; 0723
[6] Patent: EP1640360, 2006, A1, . Location in patent: Page/Page column 81
[7] Patent: WO2015/59618, 2015, A1, . Location in patent: Page/Page column 43
[8] Patent: US2010/331301, 2010, A1, . Location in patent: Page/Page column 22
  • 7
  • [ 104-88-1 ]
  • [ 411235-57-9 ]
  • [ 20034-50-8 ]
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
  • 8
  • [ 411235-57-9 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
89% With potassium phosphate monohydrate; palladium diacetate; XPhos In <i>tert</i>-butyl alcohol at 50℃; for 12 h; Schlenk technique; Inert atmosphere; Sealed tube General procedure: Procedure A: To a Schlenk tube equipped with a magnetic stiring bar and a teflon septum was charged K3PO4.H2O (1.5 mmol, 3 equiv), aryl pentafluorobenzene sulfonate (0.5 mmol, 1.0 equiv), aryl boronic acid (0.75 mmol, 1.5 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 molpercent). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inertatmosphere, tert - butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was stirred at room temperature for the time indicated. When the reaction was completed according to TLC or GCMS (FID), thereaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was concentrated under reduced pressure. The residue was purified through silica gel (230 - 400 mesh) column chromatography using 1-10percent ethyl acetate in petroleum ether to afford the product. Procedure B: Similar procedure as A except that Pd(OAc)2 (3 molpercent) and Xphos (5 molpercent) instead of Pd(PPh3)2Cl2 as catalyst system.
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 36, p. 5106 - 5111
  • 9
  • [ 90-11-9 ]
  • [ 411235-57-9 ]
  • [ 25033-19-6 ]
YieldReaction ConditionsOperation in experiment
57% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 5 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
Reference: [1] Synthetic Communications, 2006, vol. 36, # 1, p. 121 - 128
[2] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
  • 10
  • [ 121-43-7 ]
  • [ 23719-80-4 ]
  • [ 411235-57-9 ]
YieldReaction ConditionsOperation in experiment
27%
Stage #1: at -78 - 20℃;
Stage #2: With hydrogenchloride In tetrahydrofuran; water
To a stirred solution of TRIMETHYLBORATE (1.69g, 1.81 ML, 16. 25MMOL) in THF (7ML) AT-78C under a N2 atmosphere was added, by drop wise addition, cyclopropylmagnesium bromide (0.5M in THF, 25ML, 12. 5mmol). A white precipitate formed. After 1 hr the reaction was warmed to room temperature and stirred overnight. The reaction was quenched with HCI aq. (20ML, 2. ON) and the mixture stirred for 1 hour. After extracting with DCM (15ml) and back extracting with H20 (2XL5ML), the aqueous fractions were combined and extracted using TBME (4X40ML). The combined organic extracts were dried over MgS04 and concentrated under reduced pressure to give a white solid. Recrystallisation from DCM and hexane (twice) furnished a white solid 25,297mg, 27percent yield. H nmr (250MHz, CDCl3) ; 0.56-0. 50 (2H, m, CH2), 0.42-0. 40 (2H, m, CH2), -0. 08--0. 20 (1 H, m, CH).
Reference: [1] Patent: WO2004/56788, 2004, A1, . Location in patent: Page 51
  • 11
  • [ 1104637-36-6 ]
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Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
  • 12
  • [ 23719-80-4 ]
  • [ 411235-57-9 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 39, p. 6987 - 6990
  • 13
  • [ 1404118-58-6 ]
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Reference: [1] Patent: WO2005/110980, 2005, A2, . Location in patent: Page/Page column 82
  • 14
  • [ 1104637-36-6 ]
  • [ 7732-18-5 ]
  • [ 411235-57-9 ]
Reference: [1] Journal of the American Chemical Society, [2] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
  • 15
  • [ 1065010-87-8 ]
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7431 - 7441
  • 16
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 17, p. 7431 - 7441
  • 17
  • [ 464192-28-7 ]
  • [ 411235-57-9 ]
  • [ 877385-86-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 1, p. 290 - 306
  • 18
  • [ 2142-63-4 ]
  • [ 411235-57-9 ]
  • [ 408359-52-4 ]
YieldReaction ConditionsOperation in experiment
94% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 3 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
Reference: [1] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
[2] Patent: WO2016/201168, 2016, A1, . Location in patent: Paragraph 0703
[3] Patent: WO2017/214505, 2017, A1, . Location in patent: Paragraph 000559; 000560
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  • [ 103058-87-3 ]
  • [ 411235-57-9 ]
  • [ 888499-98-7 ]
Reference: [1] Patent: US2018/99932, 2018, A1, . Location in patent: Paragraph 2050
  • 20
  • [ 122433-41-4 ]
  • [ 411235-57-9 ]
  • [ 888499-96-5 ]
Reference: [1] Patent: WO2006/60108, 2006, A1, . Location in patent: Page/Page column 36; 38
  • 21
  • [ 2298-07-9 ]
  • [ 411235-57-9 ]
  • [ 878671-94-4 ]
YieldReaction ConditionsOperation in experiment
95.3% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; for 6 h; Inert atmosphere Bromo-1-naphthylamine (3) (0.50 g, 2.25 mmol), cyclopropylboronic acid (0.212 g, 2.47 mmol)Tetrakistriphenylphosphine palladium (0.26 g, 0.23 mmol), potassium phosphate (1.67 g, 7.87 mmol) was weighed out in a 50 mL round bottom flask,A mixed solvent of dioxane and water (25/1, 26 mL) was added, and the mixture was heated in an oil bath at 90 ° C. for 6 hours after being substituted by nitrogen for three times.The reaction mixture was cooled to room temperature and the insoluble material was filtered off. The solvent was evaporated under reduced pressure, 50 mL of water was added and the mixture was extracted with ethyl acetate (2 × 10 mL)The organic layer was washed twice with saturated brine, dried over anhydrous sodium sulfate and concentrated by filtration to obtain the intermediate 4.Purple-black oil, yield: 95.3percent.
83.6% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12 h; Inert atmosphere 4-bromo-1-naphthylamine II (90mmol, 20.0g), cyclopropyl boronic acid III (116mmol, 10.0g), potassium (300mmol, 64.0g) phosphate and tetrakistriphenylphosphine palladium (6mmol, 7.0g) 100mL of toluene and added to 4mL of water mixed solvent, reacted under nitrogen at 100 12h, when the reaction mixture was cooled to room temperature, the reaction mixture was added 100mL of water, extracted three times with ethyl acetate, dried over sodium sulfate was added . Half an hour later filtered by vacuum distillation to give 13.8g of intermediate compoundWas IV, a yield of 83.6percent '
83.6% With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; toluene at 100℃; for 12 h; Inert atmosphere Bromo-1-naphthylamine (10) (20.0 g, 90 mmol),Cyclopropylboronic acid (10.0 g, 116 mmol),(64.0 g, 300 mmol) and tetrakistriphenylphosphine palladium (7.0 g, 6 mmol) were added to a mixed solvent of 100 mL of toluene and 4 mL of water,And the reaction was carried out at 100 ° C for 12 hours under a nitrogen atmosphere (the reaction was complete by TLC).After completion of the reaction, the reaction solution was cooled, 100 mL of an aqueous solution was added to the reaction solution, and the mixture was extracted three times with ethyl acetate and dried over sodium sulfate. Filtered and distilled under reduced pressure to obtain 13.8 g of intermediate 4-cyclopropyl-1-naphthylamine (11) in a yield of 83.6percent.
80 g With potassium phosphate; palladium diacetate In water; toluene at 110℃; for 3 h; Inert atmosphere Example 1. 4-cyclopropyl-l-naphthylamine [066] To a four necked flask that equipped with a mechanical stirrer, a reflux condenser and a thermometer added 4-bromo-l-naphthylamine (90 g, 40.5 mmol), cyclopropyl boronic acid (38.4 g, 44.6 mmol), anhydrous potassium phosphate (258 g, 122 mmol), toluene (800 mL) and water (30 mL) to form a mixture, stirred the mixture followed by adding cyclohexylphosphine (11.5 g, 4.1 mmol) and palladium acetate (3.65 g, 1.62 mmol) under nitrogen atmosphere to form a reaction mixture. The reaction mixture was heated to 110°C and stirred at 110°C for 3 hours, then was added with water (800 mL), separated the organic layer, extracted the aqueous phase with ethyl acetate (300 mL><2) and dried the combined organic phases with anhydrous sodium sulfate. After removing the desiccant, the filtrate was reduced under vacuum pressure to obtain 4-cyclopropyl-l-naphthylamine 80 g.

Reference: [1] Chemical Biology and Drug Design, 2016, vol. 88, # 2, p. 241 - 253
[2] Patent: CN105175414, 2017, B, . Location in patent: Paragraph 0040
[3] Patent: CN105566237, 2016, A, . Location in patent: Paragraph 0060; 0061; 0062
[4] Patent: CN106083847, 2016, A, . Location in patent: Paragraph 0133; 0134; 0170; 0171
[5] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 35-36
[6] Patent: WO2014/198241, 2014, A1, . Location in patent: Paragraph 065-066
[7] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 18, p. 4424 - 4433
  • 22
  • [ 171197-80-1 ]
  • [ 411235-57-9 ]
  • [ 1034467-80-5 ]
YieldReaction ConditionsOperation in experiment
63% With potassium phosphate In water; toluene at 100℃; for 4 h; Preparation 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound (430 mg, 63 percent) as a pale yellow oil. 1H νMR (400 MHz-CDCl3) δ 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).
63% With potassium phosphate In water; toluene at 100℃; for 4 h; Preparation 145-Cyclopropyl-2-fluoro-pyridineCombine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium phosphate (3.2 g, 15 mmol) in toluene/water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 h. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound as a pale yellow oil (430 mg, 63 percent).
Reference: [1] Patent: WO2008/76705, 2008, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2008/144222, 2008, A2, . Location in patent: Page/Page column 13
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  • [ 766-11-0 ]
  • [ 411235-57-9 ]
  • [ 1034467-80-5 ]
YieldReaction ConditionsOperation in experiment
647 mg With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 80℃; for 16 h; Inert atmosphere 5-Bromo-2-fluoro - pyridine (1.41 g, 8 mmol) and cyclopropyl boronicacid (1.37 g, 16 mmol) mixed in toluene / water (26 mL / 1.3 mL), to which was added potassium phosphate (7.46 Under g, 28 mmol), argon was added theretopalladium acetate (90 mg, 0.4 mmol) and tricyclohexylphosphine (224 mg, 0.8mmol), the mixture was heated to 80  °C the reaction 16h. After completion of the reaction by TLC, cooled to room temperature,water was added thereto, extracted with ethyl acetate, the organic phase wasdried over anhydrous sodium sulfate, filtered, and the solvent was evaporatedto dryness, purified by silica gel column chromatography to give 5-cyclopropyl-2-fluoro- pyridine (yellow oil, 647 mg). 
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5579 - 5598
[2] Patent: CN103420977, 2016, B, . Location in patent: Paragraph 0229-0232
  • 24
  • [ 625-92-3 ]
  • [ 411235-57-9 ]
  • [ 1044210-57-2 ]
Reference: [1] Patent: WO2008/91681, 2008, A2, . Location in patent: Page/Page column 242
[2] Patent: US2010/16298, 2010, A1, . Location in patent: Page/Page column 205
  • 25
  • [ 288-13-1 ]
  • [ 411235-57-9 ]
  • [ 1151814-36-6 ]
Reference: [1] Patent: JP5668756, 2015, B2, . Location in patent: Paragraph 0147
  • 26
  • [ 1072-97-5 ]
  • [ 411235-57-9 ]
  • [ 893738-68-6 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With potassium phosphate In water; toluene for 0.166667 h; Inert atmosphere
Stage #2: Reflux
General procedure: The corresponding bromopyridine (1 mmol) and cyclopropylboronic acid (1.3 mmol)were dissolved in toluene (10 mL) under argon atmosphere. Then, anhydrous K3PO4 (3 mmol)and water (1 mL) were added and reaction mixture stirred for 10 min under an argon flow.Tricyclohexylphosphine (10 molpercent) and Pd(OAc)2 (5 molpercent) were added and reaction mixture stirred at reflux until GC-MS analysis of the reaction mixture indicated full consumption of thestarting material. The reaction mixture was cooled to room temperature, filtered through a pad of Celite, diluted with EtOAc (25 mL), washed with water (3 × 20 mL), dried (Na2SO4) andevaporated to dryness. The crude product was purified by column chromatography on silica gel,eluting with a methanol and CH2Cl2 mixture. 2-Amino-5-cyclopropylpyridine (1a):1 yield 85percent. Rf = 0.26 (MeOH-CH2Cl21:19). 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J = 2.4 Hz, 1H), 7.11 (dd, J =8.4, 2.4 Hz, 1H), 6.42 (d, J = 8.4 Hz, 1H), 4.19 (s, 2H), 1.80 – 1.73 (m, 1H),0.93 – 0.81 (m, 2H), 0.62 – 0.51 (m, 2H). 13C NMR (100 MHz, CDCl3) δ156.4, 146.2, 135.6, 129.0, 108.4, 12.2, 7.5. GC-MS: tR= 6.724 min (m/z (rel.in.)) 134 (64.41percent).
83% With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd In water; toluene at 100℃; for 6 h; Inert atmosphere General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol percent) was added to the solution of aryl halides (0.25 mmol) and cyclopropylboronic acid (0.5 mmol) in toluene (2.0 mL) and water (100 μL). The mixture was heated to 100 °C for a proper time under nitrogen atmosphere and cooled to room temperature. Water (10 mL) was added and the mixture was extracted with EtOAc (3.x.15 mL), evaporated and purified by chromatography on silica gel.
71% With potassium phosphate In water; toluene at 80℃; for 16 h; Inert atmosphere a) 5-Cyclopropyl-pyridin-2-ylamine; To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3PO4 (8.59 g, 40.46 mmol) under an argon atmosphere. A balloon containing argon was affixed, and the reaction flask was purged to ensure a argon atmosphere. To this were added Pd(OAc)2, (259.52 mg, 1.16 mmol) and tricyclohexylphosphene (647.3 mg, 2.3 mmol) and stirred at 80° C. for 16 h. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.1 g, 71percent).1H NMR (DMSO, 400 MHz): δ(ppm)=7.73 (s, 1H), 7.04-7.02 (dd, J=8.48 2.04 Hz, 1H), 6.34 (d, J=8.48 2.04 Hz, 1H), 5.60 (s, 2H), 1.78-1.66 (m, 1H), 0.822-0.77 (m, 2H), 0.52-0.313 (m, 2H)
71% With potassium phosphate In water; toluene at 80℃; for 16 h; Inert atmosphere To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3P04 (8.59 g, 40.46 mmol) under an argon atmosphere. A balloon containing argon was affixed, and the reaction flask was purged to ensure a argon atmosphere To this were added Pd(OAc)2, (259.52 mg,1.16 mmol) and tricyclohexylphosphene (647.3mg, 2.3mmol) and stirred at 80°C for 16 h. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (l . lg, 71percent). 1H NMR (DMSO, 400 MHz): <5 (ppm) = 7.73 (s, 1H), 7.04-7.02 (dd, J = 8.48 2.04 Hz, 1H), 6.34 (d, J = 8.48 2.04 Hz, 1H), 5.60 (s, 2H), 1.78-1.66 (m, 1H), 0.822-0.77 (m, 2H), 0.52- 0.313 (m,2H)
71% With potassium phosphate In water; toluene at 80℃; for 16 h; Inert atmosphere a) 5-Cyclopropyl-pyridin-2-ylamine; To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3PO4 (8.59 g, 40.46 mmol) under an argon atmosphere. To this were added Pd(OAc)2 (259.52 mg, 1.16 mmol) and tricyclohexylphosphene (647.3 mg, 2.3 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.1 g, 71percent).1H NMR (DMSO-D6, 400 MHz): δ (ppm)=7.73 (s, 1H), 7.04-7.02 (dd, J=8.48 2.04 Hz, 1H), 6.34 (d, J=8.48 2.04 Hz, 1H), 5.60 (s, 2H), 1.78-1.66 (m, 1H), 0.82-0.77 (m, 2H), 0.52-0.31 (m, 2H)
71% With potassium phosphate; tricyclohexylphosphine In water; toluene at 80℃; for 16 h; Inert atmosphere To a solution of 5-bromo-pyridin-2-ylamine (2 g, 11.55 mmol) and cyclopropyl boronic acid (2.98 g, 34.68 mmol) in toluene (40 mL) and water (2 mL) was added K3P04 (8.59 g, 40.46 mmol) under an argon atmosphere. To this were added Pd(OAc)2 (259.52 mg, 1.16 mmol) and tricyclohexylphosphene (647.3 mg, 2.3 mmol) and stirred at 80°C for 16 hours. The reaction mixture was cooled to room temperature and water was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (1.1 g, 71percent).1H NMR (DMSO-D6, 400 MHz): <5 (ppm) = 7.73 (s, 1H), 7.04-7.02 (dd, J = 8.48 2.04 Hz, 1H), 6.34 (d, J = 8.48 2.04 Hz, 1H), 5.60 (s, 2H), 1.78-1.66 (m, 1H), 0.82-0.77 (m, 2H), 0.52- 0.31 (m,2H)
64.47% With potassium phosphate; palladium diacetate; tricyclohexylphosphine In toluene at 110℃; for 3 h; Inert atmosphere To a solution of 5-bromopyridin-2-amine (lg, 5.78mmol, l .Oeq) in mixture of toluene (12mL) and water (lmL) were added cyclopropyl boronic acid (0.65g, 7.51mmol, 1.3eq) and potassium phosphate (2.45g, 11.56mmol, 2.0eq). The reaction mixture was degassed for 10 min under argon atmosphere, and palladium acetate (0.13g, 0.578mmol, O. leq) and Tricyclohexylphosphine (0.324g, 1.15mmol, 0.2eq) were added. Reaction mixture was again degassed for 10 min and stirred at 110°C for 3h. After completion of reaction, reaction mixture was transferred into water and extracted with ethyl acetate. Organic layer was combined, dried over sodium sulphate and concentrated under reduced pressure to obtain crude material. This was further purified by column chromatography and compound was eluted in 20percent ethyl acetate in hexane as eluent to obtain 101.1. (0.5g, 64.47 percent). MS(ES): m/z 135.18 [M+H]+
1.33 g With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 80℃; Inert atmosphere To a mixture of 5-bromopyridin-2-amine (5.0 g) in a mixed solvent of toluene (100 mL) and water (5 mL) were added cyclopropylboronic acid (4.59 g), tricyclohexyl phosphine (1.62 g), palladium(II) acetate (0.649 g) and tripotassium phosphate (21.5 g) at room temperature.
The mixture was stirred overnight at 80° C. under argon atmosphere.
The reaction mixture was allowed to be cooled to room temperature, and the insoluble substance was removed by filtration.
To the filtrate was added ethyl acetate, and the mixture was extracted with ethyl acetate.
The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (1.33 g).
1H NMR (300 MHz, DMSO-d6) δ 0.44-0.55 (2H, m), 0.72-0.86 (2H, m), 1.73 (1H, tt, J=8.4, 5.2 Hz), 5.62 (2H, s), 6.35 (1H, d, J=9.1 Hz), 7.03 (1H, dd, J=8.5, 2.5 Hz), 7.73 (1H, d, J=2.7 Hz).
1.28 g With (bis(tricyclohexyl)phosphine)palladium(II) dichloride; caesium carbonate In 1,4-dioxane for 10 h; Inert atmosphere A mixture of 2-amino-5-bromopyridine (3.00 g), cyclopropylboronic acid (2.23 g), cesium carbonate (16.9 g) and dichlorobis(tricyclohexylphosphine)palladium (1.28 g) in 1,4-dioxane (11.5 mL) was heated under reflux under a nitrogen atmosphere for 10 h
After cooling to room temperature, water was added, and the mixture was extracted twice with ethyl acetate.
The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated, and the obtained residue was purified by silica gel column chromatography (solvent; hexane/ethyl acetate=70/30 - 0/100) to give the title compound (1.28 g).
MS(ESI)m/z; 135[M+H]+

Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 17, p. 1681 - 1683
[2] Tetrahedron, 2012, vol. 68, # 3, p. 900 - 905
[3] Patent: US2011/190269, 2011, A1, . Location in patent: Page/Page column 63
[4] Patent: WO2011/92272, 2011, A1, . Location in patent: Page/Page column 132; 133
[5] Patent: US2011/201605, 2011, A1, . Location in patent: Page/Page column 43
[6] Patent: WO2011/101304, 2011, A2, . Location in patent: Page/Page column 88
[7] Patent: WO2018/71794, 2018, A1, . Location in patent: Paragraph 00567; 00568
[8] Patent: US2015/266872, 2015, A1, . Location in patent: Paragraph 0773; 0774
[9] Patent: EP3372601, 2018, A1, . Location in patent: Paragraph 0586; 0587
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  • [ 3469-69-0 ]
  • [ 411235-57-9 ]
  • [ 1239363-40-6 ]
YieldReaction ConditionsOperation in experiment
85% With pyridine; dmap; copper diacetate In 1,4-dioxane at 100℃; for 16 h; Intermediate bA. 1-Cyclopropyl-4-iodo-1H-pyrazole: To a mixture of 4-iodo- 1H-pyrazole (645 mg, 3.33 mmol), cyclopropylboronic acid (571 mg, 6.65 mmol), copper(II) acetate (604 mg, 3.33 mmol) and DMAP (1219 mg, 9.98 mmol) in dioxane (10mL) was added pyridine (0.323 mL, 3.99 mmol). The resulting mixture was heated to 100°C for 1 6h under air. The reaction mixture was concentrated in vacuo and diluted withEtOAc. The organic layer was washed with 1M HC1. The organic layer was dried overMgSO4, filtered and concentrated in vacuo. The crude product was purified bychromatography to give Intermediate 1OA (660 mg, 2.82 mmol, 85percent yield) as a lightyellow liquid. LCMS Anal. Calc’d for C6H7N2 234.04, found [M+H] 234.9.
43% With [2,2]bipyridinyl; copper diacetate; sodium carbonate In 1,2-dichloro-ethane at 50 - 70℃; Step 1
In a flask were combined 4-iodo-1H-pyrazole (1.00 g, 5.16 mmol), cyclopropylboronic acid (886 mg, 10.3 mmol) and sodium carbonate (1.09 g, 10.3 mmol) and the mixture suspended in 1,2-dichloroethane (20 mL).
A suspension of copper (II) acetate (936 mg, 5.16 mmol) and 2,2-bipyridine (805 mg, 5.16 mmol) in 1,2-dichloroethane (40 mL) was warmed to 50° C. and added and the resulting mixture heated at 70° C. overnight.
The mixture was then cooled and filtered and the solids rinsed with EtOAc.
The combined filtrates were concentrated and the residue taken up in EtOAc and 50percent saturated aqueous NH4Cl.
The organic layer was washed with sat NH4Cl, sat NaHCO3 and sat NaCl and dried over MgSO4.
The solution was concentrated and the residue purified by SiO2 chromatography (5-35percent EtOAc/heptane) to afford 517 mg (43percent) 1-cyclopropyl-4-iodo-1H-pyrazole as a colorless oil.
Reference: [1] Patent: WO2015/134701, 2015, A1, . Location in patent: Page/Page column 58
[2] Patent: US2011/230462, 2011, A1, . Location in patent: Page/Page column 84
  • 28
  • [ 78607-36-0 ]
  • [ 411235-57-9 ]
  • [ 865664-04-6 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 120℃; for 4 h; To a mixture of 2-chloro-3-iodopyridine (2.39 g, 9.98 mmol), cyclopropylboronic acid (860 mg, 10 mmol) and potassium carbonate (4.14 g, 30.0 mmol) in 1 ,4-dioxane (50 mL) was added tetrakis(triphenylphosphine)palladium(0) (1 .16 g, 1 .00 mmol). The reaction mixture was stirred at 120 °C for 4 hours, then diluted with ethyl acetate (50 mL) and filtered. The filtrate was concentrated and the residue was purified by silica gel chromatography (Gradient: 10percent to 30percent ethyl acetate in petroleum ether) to afford the product as a colorless oil. Yield: 1 g, 6 mmol, 60percent. 1 H NMR (400 MHz, CDCl3) δ 8.20 (dd, J=4.7, 1.8 Hz, 1 H), 7.24-7.28 (m, 1 H), 7.14 (br dd, J=7.6, 4.8 Hz, 1 H), 2.12-2.21 (m, 1 H), 1.04-1.11 (m, 2H), 0.67-0.72 (m, 2H).
Reference: [1] Patent: WO2014/207601, 2014, A1, . Location in patent: Page/Page column 70; 72
  • 29
  • [ 13535-01-8 ]
  • [ 411235-57-9 ]
  • [ 1314353-68-8 ]
YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 15 h; To a solution of 5-bromopyridin-3-amine (4.75 g, 27.45 minol) in dioxane (45 mL) was added cyclopropylboronic acid (4.75 g, 55.30 minol), C52CO3(28 g, 85.67 minol), tetrakis(triphenylphosphane) palladium(1.66 g, 1.44 minol) and water (5 mL) at room temperature. The resultingminxture was then stirred for 15 h at 100 °C. After cooling to room temperature, the reaction mxiture was diluted with water (200 mL). The resultingminxture was extracted with ethyl acetate (500 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0percent to 100percent gradient) to yield 5-cyclopropylpyridin-3-amine as light brown oil (2.08 g, 56percent). MS: m/z = 135.0 [M+Hj .
314 mg With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; for 5 h; Inert atmosphere; Sealed tube Reference Example 45
Cyclopropylboronic acid (360 mg), cesium carbonate (1.4 g), and Pd(PPh3)4 (166 mg) were added to a 1,4-dioxane/water (4.5 ml/0.5 ml) solution containing 5-bromopyridin-3-amine (500 mg) in a nitrogen atmosphere, followed by stirring in a sealed tube at 100° C. for 5 hours.
The reaction solution was adjusted to room temperature and water was added to the reaction solution, followed by extraction with ethyl acetate.
The organic layers were washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and the obtained residue was purified by silica gel chromatography (chloroform:MeOH=1:0 to 30:1).
A brown solid of 5-cyclopropyl pyridin-3-amine (314 mg) was thus obtained.
MS (ESI m/z): 135 (M+H)
Reference: [1] Patent: WO2017/106607, 2017, A1, . Location in patent: Paragraph 00477
[2] Patent: EP2762476, 2014, A1, . Location in patent: Paragraph 0174
[3] Patent: US2014/309225, 2014, A1, . Location in patent: Paragraph 0700; 0701; 0702; 0703
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