Name: Cyclopropylboronic acid
Brand: Ambeed
SKU: A444176

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Quality Control of Cyclopropylboronic acid Purity: 96% GC SDS Specification

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Product Details of Cyclopropylboronic acid

CAS No. :	411235-57-9
Formula :	C₃H₇BO₂
M.W :	85.90
SMILES Code :	OB(C1CC1)O
MDL No. :	MFCD04038750
InChI Key :	WLVKDFJTYKELLQ-UHFFFAOYSA-N
Pubchem ID :	2760897

Safety of Cyclopropylboronic acid

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Cyclopropylboronic acid

* 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 1~1

1
[ 2142-63-4 ]
[ 411235-57-9 ]
[ 408359-52-4 ]

Yield	Reaction Conditions	Operation 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.

References: [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.

[ 411235-57-9 ] Synthesis Path-Downstream 1~35

1
[ 86-86-2 ]
[ 411235-57-9 ]
[ 694518-58-6 ]

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 6441 - 6444.

2
[ 53312-82-6 ]
[ 411235-57-9 ]
[ 1006899-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;bis-triphenylphosphine-palladium(II) chloride; In ethanol; water; toluene; at 80℃; for 19h;	To a stirred mixture of <strong>[53312-82-6]4-amino-2-bromobenzonitrile</strong> (2.00 g, 10.2 mmol), cyclopropyl boronic acid (1,18 g, 13.7 mmol) and K3PO4 (3.23 g, 15.2 mmol) in the mixed solvents of EtOH/H2O/toluene (2 mL/2 mL/12 mL) under nitrogen was added PdCl2(PPh3)2 (0.72 g, 1.03 mmol). This mixture was heated at 800C for 19 h and cooled to room temperature. Next, the mixture was diluted with 150 mL of EtOAc and filtered through a pad of silica gel topped with a layer of celite. This pad was further rinsed with EtOAc (2 x 100 mL). The filtrate was washed with 25 mL of brine, dried over MgSO4, filtered and concentrated in vacuo to give the crude amine. The crude amine was purified by an ISCO auto flash chromatographer using 12O g silica gel column, eluted with hexanes/CH2Cl2 solvents in a 25 min 50% to 100% gradient elution to give 0.75 g of Preparation 4OA as a white solid in 47% yield. [00428] HPLC: 1.55 min (RT) (Chromolith SpeedROD column 4.6 x 50 mm, 10- 90% aqueous MeOH over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm). MS (ES): m/z=159 [M+H]+. 1H NMR of 4-amino-2- cyclopropyl-benzonitrile (400 MHz, CDCl3) delta ppm 7.34 (d, J=8.31 Hz, 1 H) 6.44 (dd, J=8.31, 2.27 Hz, 1 H) 6.12 (d, J=2.01 Hz, 1 H) 4.01 (s, 2 H) 2.13-2.24 (m, 1 H) 1.02- 1.12 (m, 2 H) 0.68-0.76 (m, 2 H).

References: [1]Patent: WO2009/3077,2008,A1 .Location in patent: Page/Page column 116.

3
[ 171663-13-1 ]
[ 411235-57-9 ]
[ 1108723-65-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate;palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 3h;	Example 1.1.22: (3-cyclopropylphenyl)methanamine; To a solution of <strong>[171663-13-1]tert-butyl 3-bromobenzylcarbamate</strong> (572 mg, 2 mmol), cyclopropyl boronic acid (223 mg, 2.6 mmol), potassium phosphate (1.49 g, 7.0 mmol) and tricyclohexyl phosphine (56 mg, 0.2 mmol)in toluene (9 mL) and water (0.45 mL) under a nitrogen atmosphere was added palladium acetate (22mg, 0.1 mmol). The mixture was heated at 1000C for 3h and then cooled to rt. Water (20 mL) was added and the mixture extracted with EtOAc (2x30 mL), the combined organic extracts were washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. Crude product was purified by column chromatography (15% EtOAc in hexanes) afforded tert-butyl 3-cyclopropylbenzylcarbamate as a colorless oil in 93% yield. (3-cyclopropylphenyl)methanamine was then generated by removing the Boc protecting group by treatment with HCl (in methanol or dioxane) or trifluoroacetic acid in dichloromethane.

References: [1]Patent: WO2009/42694,2009,A1 .Location in patent: Page/Page column 81.

4
[ 154258-82-9 ]
[ 411235-57-9 ]
[ 1286230-88-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With pyridine; triethylamine; In tetrahydrofuran; for 18h;Reflux;	1-Cyclopropyl-<strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> [XX-1]; A mixture of 10 g of <strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> (62 mmol), 10.59 g of cyclopropylboronic acid (123 mmol), 44 mL triethylamine (308 mmol) and 40 mL pyridine (493 mmol) in dry THF is heated under reflux for 18 hrs. Next the reaction mixture is cooled, filtered over Celite and concentrated. The residue is taken up in ethyl acetate, washed with Na2CO3 solution, dried and evaporated under vacuum. The crude product is chromatographed over silica gel and 5 g (40%) of 1-cyclopropyl-<strong>[154258-82-9]3-(4-fluorophenyl)-1H-pyrazole</strong> are obtained.MS (ESI): 203.0 ([M+H]+)1H-NMR (400MHz, CDCl3) delta=7.76-7.73 (m, 2H) 7.435 (d, J=2.04 Hz, 1H), 7.05 (t, J=8.6 Hz, 2H), 6.44 (s, 1H), 3.64-3.58 (m, 1H), 1.24-1.14 (m, 2H), 1.06-1.01 (m, 2H) ppm
39.5%	With pyridine; dmap; copper diacetate; In 1,4-dioxane; at 100℃;	Intermediate 3 A was prepared according to the procedures described in Org. Lett., 1653-1655 (2008). To a solution of 3-(4-fluorophenyl)-lH-pyrazole (6.5 g, 40.1 mmol) in dioxane (80 mL) were added cyclopropylboronic acid (7.26 g, 85 mmol), DMAP (14.7 g, 120 mmol), diacetoxycopper (7.28 g, 40.1 mmol), and pyridine 3.24 mL, 40.1 mmol). The reaction mixture was heated at 100 C overnight. The reaction mixture was cooled to rt, quenched with water, and extracted with EtOAt. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by BIOTAGE (90g Thomson, 0-40% EtOAc/hex) to give Intermediate 3 A (3.2 g, 39.5%) as a tan oil. MS(ES): m/z= 203.13 [M+H]+. HPLC Ret time (Method B): 3.52 min. XH NMR (400MHz, chloroform-d) delta 7.84 - 7.72 (m, 2H), 7.13 - 7.01 (m, 2H), 6.46 (d, J=2.3 Hz, 1H), 3.63 (dt, J=7.2, 3.5 Hz, 1H), 1.21 - 1.11 (m, 2H), 1.11 - 0.90 (m, 2H).

References: [1]Patent: US2011/183978,2011,A1 .Location in patent: Page/Page column 58.
[2]Patent: WO2014/100540,2014,A1 .Location in patent: Page/Page column 56-57.

5
[ 411235-57-9 ]
[ 820236-81-5 ]
[ 1352133-13-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 2.5h;Inert atmosphere; Reflux;	Step 2: Synthesis of methyl 2-cyclopropyl-6-fluorobenzoate (3).[00365] Methyl 2-bromo-6-fluorobenzoate (2, 11.29 g, 48.5 mmol), cyclopropylboronic acid (6.24 g, 72.7 mmol), K3PO4 (30.85 g, 145.4 mmol) and Pd(PPh3)4 (2.80 g, 2.4 mmol) were mixed under argon in a degassed mixture of toluene and water (20:1, 160 mL). The resulting brown suspension was heated at reflux for 2.5 h, cooled, filtered through Celite, and evaporated. The residue was partitioned between ethyl acetate (150 mL) and brine (150 mL). The layers were separated and organic layer was dried over magnesium sulfate and evaporated. The oily residue was suspended in hexane and the solid was removed by filtration. Evaporation of the filtrate afforded the title compound (9.30 g, 47.9 mmol, 99%) as a light brown oil.
99%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 2.5h;Inert atmosphere; Reflux;	[00500] Methyl 2-bromo-6-fluorobenzoate (38) (11.29 g, 48.5 mmol), cyclopropylboronic acid (6.24 g, 72.7 mmol), K3P04 (30.85 g, 145.4 mmol) and Pd(PPh3)4 (2.80 g, 2.4 mmol) were mixed under argon in a degassed mixture of toluene and water (20: 1, 160 mL). The resulting brown suspension was heated at reflux for 2.5 h, cooled, filtered through Celite, and evaporated. The residue was partitioned between ethyl acetate (150 mL) and brine (150 mL). The layers were separated and organic layer was dried over magnesium sulfate and evaporated. The oily residue was suspended in hexane and the solid was removed by filtration. Evaporation of the filtrate afforded the title compound (9.30 g, 47.9 mmol, 99%) as a light brown oil.

References: [1]Patent: WO2011/156786,2011,A2 .Location in patent: Page/Page column 128.
[2]Patent: WO2013/86451,2013,A2 .Location in patent: Paragraph 00500.

6
[ 26163-07-5 ]
[ 411235-57-9 ]
[ 1245645-43-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium phosphate tribasic heptahydrate; C45H53ClFeNO2PPd; In water; toluene; at 100℃; for 6h;Inert atmosphere;	General procedure: Potassium phosphate (0.75 mmol) and IIe (1 mol %) 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 muL). 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 (3×15 mL), evaporated and purified by chromatography on silica gel.

References: [1]Tetrahedron,2012,vol. 68,p. 900 - 905.

7
[ 16115-08-5 ]
[ 411235-57-9 ]
[ 1362054-25-8 ]

References: [1]Synthetic Communications,2012,vol. 42,p. 1341 - 1348.

8
[ 411235-57-9 ]
[ 56844-12-3 ]
[ 439692-99-6 ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium carbonate; triphenylphosphine;palladium diacetate; In water; toluene; at 110℃;Inert atmosphere;	Example 106. Synthesis of 4-N-[6-cycIopropylthieno[2,3-d]pyrimidin-4-yl]-l-N,l- N-dimethylcyclohexane-l,4-diamine (1-184).Page 195 of 4072009184-0008 1-184[00498] Synthesis of 4-chloro-6-cyclopropylthieno[2,3-d]pyrimidine. A 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was charged with commercially available <strong>[56844-12-3]6-bromo-4-chlorothieno[2,3-d]pyrimidine</strong> (1.5 g, 6.01 mmol, 1.00 equiv), cyclopropylboronic acid (1.2 g, 13.97 mmol, 2.30 equiv), sodium carbonate (2.16 g, 20.38 mmol, 3.40 equiv), PPh3 (552 mg, 2.10 mmol, 0.35 equiv), Pd(OAc)2 (162 mg, 0.72 mmol, 0.12 equiv), water (7.5 mL) and methylbenzene (22.5 mL). The resulting solution was stirred overnight at 110 C in an oil bath. The resulting solution was diluted with 50 mL of water. The resulting solution was extracted with 3 x 100 mL of dichloro methane and the organic layers combined. The resulting mixture was washed with 3 x 200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 : 15-1 :5). This resulted in 400 mg (32%) of 4-chloro-6-cyclopropylthieno[2,3-d]pyrimidine as a yellow solid.[00499] Synthesis of Compound 1-184. A 50-mL round-bottom flask was charged with 4- chloro-6-cyclopropylthieno[2,3-d]pyrimidine (400 mg, 1.90 mmol, 1.00 equiv), 1-N, 1-N- dimethylcyclohexane-l,4-diamine (324 mg, 2.28 mmol, 1.20 equiv) and potassium carbonate (393 mg, 2.84 mmol, 1.50 equiv) in N,N-dimethylformamide (10 mL). The resulting solution was stirred for 48 h at 45 C in an oil bath. The resulting solution was diluted with 150 mL of water. The resulting solution was extracted with 3 x 200 mL of dichloromethane and the organic layers combined. The resulting mixture was washed with 3 x 300 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by preparative HPLC (2No.- Waters 2767-2(HPLC-08)) under the following conditions: column: Xbridge Prep Phenyl, 5um, 19* 150mm; mobile phase: water (50 mM NH4HCO3) and CH3CN (10.0% CH3CN up to 33.0% in 2 min, up to 53.0% in 8 min, up to 100.0% in 1 min, down to 10.0% in 1 min); detector: UV 220 nm. This resulted in 43.3 mg (7%) of Compound 1-184 as a white solid. NMR: (400 MHz, CDC13) delta 8.41 (1H, s), 6.73 (1H, s), 4.77-4.75 (2H, d), 4.15- 4.05 (1H, m), 2.35 (6H, s), 2.31-2.27 (2H, d), 2.17-2.07 (1H, m), 2.01-1.96 (2H, d), 1.56-1.42Page 196 of 4072009184-0008 (2H, m). 1.34-1.21 (3H, m), 1.1 1-1.04 (2H, m), 0.78-0.85 (2H, m). MS: m/z 317 (M+H)+.

References: [1]Patent: WO2012/97013,2012,A1 .Location in patent: Page/Page column 195-197.

9
[ 3177-20-6 ]
[ 411235-57-9 ]
[ 1401350-08-0 ]

Yield	Reaction Conditions	Operation in experiment
26%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In tetrahydrofuran; for 4h;Inert atmosphere; Reflux;	To a solution of <strong>[3177-20-6]methyl 2,4-dichloropyrimidine-5-carboxylate</strong> (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL X 3). The organic layers were dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26percent yield) as a white solid.
26%	In tetrahydrofuran; water;	(S)-(4-cyclopropyl-2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2 (1H)-yl)pyrimidin-5-yl)methanol To a solution of <strong>[3177-20-6]methyl 2,4-dichloropyrimidine-5-carboxylate</strong> (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1 g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL*3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26percent yield) as a white solid.
26%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere; Reflux;	To a solution of <strong>[3177-20-6]methyl 2,4-dichloropyrimidine-5-carboxylate</strong> (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL X 3). The organic layers were dried over anhydrous Na2S04, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26percent yield) as a white solid.

26%

In tetrahydrofuran; water;

Example 20 (R)-(4-cyclopropyl-2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)pyrimidin-5-yl)methanol and (S)-(4-cyclopropyl-2-(8-(hydroxymethyl)-1-isopropyl-7-(methylsulfonyl)-3,4-dihydrobenzo[4,5]imidazo[1,2-a]pyrazin-2(1H)-yl)pyrimidin-5-yl)methanol To a solution of <strong>[3177-20-6]methyl 2,4-dichloropyrimidine-5-carboxylate</strong> (852 mg, 4 mmol) and cyclopropylboronic acid (344 mg, 4 mmol) in THF (10 mL) was added K3PO4 (3.1 g, 12 mmol) followed by Pd(dppf)Cl2 (292 mg, 0.4 mmol) under N2. The mixture was refluxed for 4 h until the material was disappeared. The reaction mixture was cooled to rt. THF was removed under vacuum. Water (20 mL) was added and the mixture was extracted with EtOAc (20 mL*3). The organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by preparative TLC to afford methyl 2-chloro-4-cyclopropylpyrimidine-5-carboxylate (220 mg, 26percent yield) as a white solid.

References: [1]Patent: WO2013/138568,2013,A1 .Location in patent: Page/Page column 93.
[2]Patent: US2015/250787,2015,A1 .
[3]Patent: WO2015/195922,2015,A1 .Location in patent: Paragraph 00188.
[4]Patent: US2016/113930,2016,A1 .

10
[ 685892-23-3 ]
[ 411235-57-9 ]
[ 1561771-86-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;Inert atmosphere;	Step 1. Preparation of methyl 2-chloro-6-cyclopropylbenzoate (i-Sb).Methyl 2-bromo-6-chlorobenzoate (i-5a) (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3P04 (2.5 g, 12.0mmol) were mixed in toluene (20 ml) and H20 (2.5 ml). The mixture was stirred at 100C overnight under N2 atmosphere. The mixture was cooled down and poured into water (50 ml). The mixture was extracted with EA (50 ml). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography(PetroleumlEtOAc 15/1) to give 0.6 g (7 1%) of the title compound. LCMS (ESI) calc?d for C11H11C102 [M+H]: 211, found: 211.
71%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene;Inert atmosphere;	Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3P04 (2.5 g, 12.0mmol) were stirred overnight in toluene (20 ml) and H20 (2.5 ml) under an atmosphere of N2(g). The mixture was cooled to room temperature and poured into water (50 ml). The mixturewas then extracted with EA (50 ml). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (PetroleumlEtOAc 15/1) to give 0.6 g (71%) of the title compound. LCMS (ESI) calc?d for C11H11C102 [M+H]: 211, found: 211.
71%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;Inert atmosphere;	Step 1. Preparation of methyl 2-chloro-6-cyclopropylbenzoate (i-5b) [0272] Methyl 2-bromo-6-chlorobenzoate (i-5a) (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 ml) and H2O (2.5 ml). The mixture was stirred at 100 C. overnight under N2 atmosphere. The mixture was cooled down and poured into water (50 ml). The mixture was extracted with EA (50 ml). The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc 15/1) to give 0.6 g (71%) of the title compound. LCMS (ESI) calc'd for C11H11ClO2 [M+H]+: 211. found: 211.

52%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;Inert atmosphere;	Methyl 2-bromo-6- chlorobenzoate (i-lb) (0.8 g, 3.2 mmol), cyclopropylboronic acid (330 mg, 3.84 mmol), Pd(OAc)2 (72 mg, 0.32 mmol), Cy3P (180 mg, 0.64 mmol) and K3P04 (2.0 g, 9.6 mmol) were mixed in toluene (12 ml) and H20 (1.2 ml). The reaction mixture was stirred at 100 C for overnight under N2 atmosphere. After cooled, the mixture was poured into water (30 ml) and extracted with EA (50 ml). The organic layer was dried over Na2S04 and concentrated to obtain a residue. The residue was purified by chromatography on silica gel (PE/EA=10: 1) to obtain 350 mg (52%) of the title compound. LCMS (ESI): calc'd for CnHnC102 [M+H] : 211, found: 211.
52%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;Inert atmosphere;	Methyl 2-bromo-6-chlorobenzoate (i-lb) (0.8 g, 3.2 mmol), cyclopropylboronic acid (330 mg, 3.84 mmol), Pd(OAc)2 (72 mg, 0.32 mmol), Cy3P (180 mg, 0.64 mmol) and K3PO4 (2.0 g, 9.6 mmol) were mixed in toluene (12 ml) and H20 (1.2 ml). The reaction mixture was stirred at 100 C overnight under N2 atmosphere. After cooling, the mixture was poured into water (30 ml) and extracted with EA (50 ml). The organic layer was dried over Na2SO4 and concentrated to obtain a residue. The residue was purified by chromatography on silica gel (PE/EA=10:1) to obtain 350 mg (52%) of the title compound. LCMS (ESI): calc?d for C11H11C102 [M+H]:211, found: 211.
	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 14h;Inert atmosphere;	Step 1. Preparation of methyl 2-chloro-6-cvclopropylbenzoate (i-la) [00137] Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P ( 224 mg, 0.8 mmol) and K3PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 mL) and H2O (2.5 mL). The mixture was stirred at 100C for 14h under N2 atmosphere. The mixture was cooled down and poured into water. The mixture was extracted with EtOAc and the organic layer was dried over Na2SC>4 and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc 15/1) to give the title compound. MS: 211 (M+l).
	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 14h;Inert atmosphere;	Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 ml) and H2O (2.5 ml). The mixture was stirred at 100 C. for 14 h under N2 atmosphere. The mixture was cooled down and poured into water. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc 15/1) to give title compound. LCMS (ESI) calc'd for CHHHClO2 [M+H]+: 211, found: 211.
	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 14h;Inert atmosphere;	Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 mL) and H2O (2.5 mL). The mixture was stirred at 100 C. for 14 h under N2 atmosphere. The mixture was cooled down and poured into water. The mixture was extracted with EtOAc and the organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (Petroleum/EtOAc 15/1) to give the title compound. MS: 211 (M+1).
	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 14h;Inert atmosphere;	Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0 mmol), Pd (OAc) 2 (90 mg, 0.4mmol), Cy3 P (224 mg, 0.8 mmol) and K3 PO4 (2.5 g, 12.0 mmol) were mixed in toluene (20 mL) and H2 O (2.5 mL). The mixture was stirred under N 2 atmosphere at 100 C. for 14 hours. The mixture was cooled and poured into water. The mixture was extracted with EtOAc and the organic layer was dried over Na 2 SO 4 and concentrated. The residue was purified by flash chromatography (petrol / EtOAc 15/1) to give the title compound.

References: [1]Patent: WO2014/28597,2014,A2 .Location in patent: Page/Page column 46; 47.
[2]Patent: WO2014/28589,2014,A2 .Location in patent: Page/Page column 72.
[3]Patent: US2015/191434,2015,A1 .Location in patent: Paragraph 0272.
[4]Patent: WO2014/26327,2014,A1 .Location in patent: Page/Page column 52-53.
[5]Patent: WO2014/28589,2014,A2 .Location in patent: Page/Page column 56; 57.
[6]Patent: WO2017/75182,2017,A1 .Location in patent: Paragraph 00137.
[7]Patent: US2018/16239,2018,A1 .Location in patent: Paragraph 0178; 0179.
[8]Patent: US2018/305320,2018,A1 .Location in patent: Paragraph 0154; 0155.
[9]Patent: JP2018/531957,2018,A .Location in patent: Paragraph 0019.

11
[ 685892-23-3 ]
[ 411235-57-9 ]
[ 1561771-92-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; palladium diacetate; In water; toluene; at 100℃; for 14h;Inert atmosphere;	Step 1. Preparation of methyl 2-chloro-6-cyclopropylbenzoate (i-9a).Methyl 2-bromo-6-chlorobenzoate (1.0 g, 4.0 mmol), cyclopropylboronic acid (516 mg, 6.0mmol), Pd(OAc)2 (90 mg, 0.4 mmol), Cy3P (224 mg, 0.8 mmol) and K3P04 (2.5 g, 12.0mmol) were mixed in toluene (20 ml) and H20 (2.5 ml). The mixture was stirred at 100C for14h under N2 atmosphere. The mixture was cooled down and poured into water (50 ml). The mixture was extracted with EtOAc (50 ml). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (PetroleumlEtOAc 15/1) to give 0.6 g (71%) of the title compound. LCMS (ESI) calc?d for C11H11C102 [M+H]: 211,found:211.

References: [1]Patent: WO2014/28600,2014,A2 .Location in patent: Page/Page column 47.

12
[ 1351813-02-9 ]
[ 411235-57-9 ]
6-bromo-1-cyclopropyl-5-nitro-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42.91%	With [2,2]bipyridinyl; copper acetylacetonate; sodium carbonate; In 1,2-dichloro-ethane; at 80℃; for 2h;Sealed tube; Inert atmosphere;	A solution of 6-bromo-2-cyclopentyl-5-nitro-2H-indazole (0.300 g, 0.967 mmol) (product of step 3 in example 5) in toluene:H20 (12 mL, 3:1), cyclopropyl boronic acid (0.124 g, 1.45 mmol), Pd2(dba)3 (10 mg, 0.009 mmol), potassium carbonate (0.300 g, 2.901 mmol) andtricyclohexyl phosphine (16 mg, 0.058 mmol) were taken in a sealed tube under nitrogen atmosphere. The contents were heated at 90 C for 12 h, cooled to room temperature and filtered through Celite. The filtrate was diluted with ethyl acetate and the organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain crude compound. The residue was purified by column chromatography (n-hexane:EtOAc;7:3) to give the title compound (0.160 g, 61 %) as a light brown solid.?H NMR (400 MHz, DMSO-d6):oe8.69 (s, 1H), 8.43 (s, 1H), 7.50 (s, 1H), 5.12-5.05 (m, 1H), 2.33-2.20 (m, 3H), 2.19-2.01 (m, 2H), 1.93-1.83 (m, 2H), 1.75-1.65 (m, 2H), 0.94-0.79 (m, 2H),0.73-0.69 (m, 2H). LCMS: mlz: 272 (M+1).Using the same reagents and conditions as described in step 1 of example 6, 6-bromo-5- nitro-1H-indazole (product of step 2 of example 5) (1gm, 4. 1322mmo1) was coupled with cyclopropyl boronic acid (7 10mg, 8.2644mmo1) using Cu(OAc)2 (901mg, 4.9586 mmol), 2,2-bipyridine (775mg, 4.9586mmo1) and sodium carbonate (1.314gm, 12.3966 mmol) in dichloroethane (20 mL) at 80C for 2h to get the crude compound. This was purified by silica gel column chromatography and elution with 1% methanol in DCM gave the title compound (500mg, 42.91%).?HNMR (CDC13, 300MHz): oe 8.34 (s, 1H), 8.07 (s, 1H), 7.95 (s, 1H), 3.64-3.57 (m, 1H), 1.25-1.24 (m, 4H). LCMS: 89.33%, mlz = 281.9 (M+1) .
42.91%	With [2,2]bipyridinyl; copper diacetate; sodium carbonate; In dichloromethane; at 80℃; for 2h;Sealed tube; Inert atmosphere;	A solution of 6-bromo-2-cyclopentyl-5-nitro-2H-indazole (0.300 g, 0.967 mmol) (product of step 3 in example 5) in toluene:H2O (12 mL, 3:1), cyclopropyl boronic acid (0.124 g, 1.45 mmol), Pd2(dba)3 (10 mg, 0.009 mmol), potassium carbonate (0.300 g, 2.901 mmol) and tricyclohexyl phosphine (16 mg, 0.058 mmol) were taken in a sealed tube under nitrogen atmosphere. The contents were heated at 90 C. for 12 h, cooled to room temperature and filtered through Celite. The filtrate was diluted with ethyl acetate and the organic layer was washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain crude compound. The residue was purified by column chromatography (n-hexane:EtOAc; 7:3) to give the title compound (0.160 g, 61%) as a light brown solid; Using the same reagents and conditions as described in step 1 of example 6, <strong>[1351813-02-9]6-bromo-5-nitro-1H-indazole</strong> (product of step 2 of example 5) (1 gm, 4.1322 mmol) was coupled with cyclopropyl boronic acid (710 mg, 8.2644 mmol) using Cu(OAc)2 (901 mg, 4.9586 mmol), 2,2'-bipyridine (775 mg, 4.9586 mmol) and sodium carbonate (1.314 gm, 12.3966 mmol) in dichloroethane (20 mL) at 80 C. for 2 h to get the crude compound. This was purified by silica gel column chromatography and elution with 1% methanol in DCM gave the title compound (500 mg, 42.91%). 1HNMR (CDCl3, 300 MHz): delta 8.34 (s, 1H), 8.07 (s, 1H), 7.95 (s, 1H), 3.64-3.57 (m, 1H), 1.25-1.24 (m, 4H). LCMS: 89.33%, m/z=281.9 (M+1)+.

References: [1]Patent: WO2015/104662,2015,A1 .Location in patent: Page/Page column 46; 72.
[2]Patent: US2016/326151,2016,A1 .Location in patent: Paragraph 0251; 0252; 0382; 0283.

13
[ 43192-34-3 ]
[ 411235-57-9 ]
4-cyclopropyl-3-methoxy-benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.3 g	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene;Inert atmosphere;	To a mixture of 4-bromo-3-methoxy-benzaldeyde (5.0 g, 23.38 mmol), cyclopropylboronic acid (3 g, 35 mmol) and potassium phosphate (17.3 g, 81.83 mmol) in toluene (100 mL) was added water (10 mL), tricyclohexylphosphine (0.65 g, 2.33 mmol) and palladium (II) acetate (260 mg, 1.16 mmol). The reaction mixture was heated at reflux under argon atmosphere overnight. The reaction was cooled, and then diluted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to give 4-cyclopropyl-3-methoxy-benzaldehyde (3.3 g).
3.3 g	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene;Inert atmosphere; Reflux;	Step 1: Preparation of 4-eyelopropyI-3-methoxy-benzaIdehyde To a mixture of 4-bromo-3-methoxy-benzaldeyde (5.0 g, 23.38 mmol), cyclopropylboronic acid (3 g, 35 mmol) and potassium phosphate ( 17.3 g, 81.83 mmol) in toluene ( 100 ml.) was addcd water ( 1 0 mL), tricyclohexylphosphine (0.65 g, 2.33 mmol) and palladium ( I I ) acetate (260 mg. 1 . 1 6 mmol). The react ion mixture was heated at reflux under argon atmosphere overnight. The reaction was cooled, and then diluted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by column chromatography to give 4- cyelopropyl-3-mcthoxy-benzaldehydc (3.3 g).

References: [1]Patent: US2015/210682,2015,A1 .Location in patent: Paragraph 1238; 1239.
[2]Patent: WO2015/113990,2015,A1 .Location in patent: Page/Page column 160; 161.

14
[ 25475-67-6 ]
[ 411235-57-9 ]
[ 1400701-71-4 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 4h;Inert atmosphere;	A mixture of the compound obtained in (1) (5.74 g,25.7 mmol), cyclopropylboronic acid (6.63 g, 77.2 mmol), tricyclohexylphosphine (1.44 g, 5.13 mmol), palladium(II) acetate (578 mg, 2.57 mmol), and tripotassium phosphate (19.1 g, 90.0 mmol) in. toluene (130 ml,) and water (6.5 mE) was stirred at 100° C. for 4 hours under argon atmosphere. To the reaction mixture were added water and ethyl acetate, insoluble material was filtered off, and the filtrate was washed with saturated saline. The organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained brown oil was purified by an NH silica gel column chromatography (hexane:chloroform=70:30? 0:100). The obtained yellow solid was suspended in a mixed solvent of ethyl acetate and diisopropylether, stirred, and then collected by filtration to give 4-cyclopropylisoquinoline-3-amine (3.11 g, 66percent) as a pale yellow solid.APCI-MS mlz: 185 [M+H]

References: [1]Patent: US2015/307454,2015,A1 .Location in patent: Paragraph 0540; 0542; 0543.

15
[ 676448-17-2 ]
[ 411235-57-9 ]
C₁₆H₁₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.29%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃; for 4h;	In a degassed suspension of compound 2 (2.000 g, 6.753 mmol), cyclopropylboronic acid (0.754 g, 8.78 mmol), K3PO4 (5.017 g, 23.64 mmol) and tricyclohexyl phosphine (0.189 g, 0.675 mmol) in toluene (60.0 mL) and water (2.0 mL) was added palladium (II) acetate (0.076 g, 0.34 mmol). The reaction mixture was heated at 100 C. for 4 h. The reaction progress was monitored by diluting an aliquot of the reaction mixture with water and extracting with EtOAc. The organic layer was spotted over an analytical silica gel TLC plate and visualized using 254 nm UV light. The reaction progressed to completion with the formation of a polar spot. The Rf values of the starting material and product were 0.3 and 0.2, respectively. The reaction mixture was allowed to cool to rt and filtered through a pad of celite, and the filtrate was concentrated under reduced pressure to afford crude compound. The crude compound was purified by flash column using 230-400 mesh silica gel and eluted with 10% EtOAc in petroleum ether to afford compound 2 as a brown liquid. TLC system: 5% EtOAc in petroleum ether. Yield 1.100 g (63.29%).

References: [1]Patent: US2016/9706,2016,A1 .Location in patent: Paragraph 0316.

16
[ 7746-27-2 ]
[ 411235-57-9 ]
C₁₁H₁₁BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: i) Alkylation via Chan-Lam coupling (5a):[0006741 To a stirred solution of compound 4 (1 eq) and corresponding boronic acid in dichloroethane, Na2CO3 (2 eq) was added under oxygen atmosphere and stirred for 5 mm followed by the addition of hot solution of copper acetate (1 eq) and pyridine (1 eq) in dichloroethane. The reaction mixture was heated to 75 C for 18 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated ammonium chloride solution, diluted with dichloromethane and filtered through celite. The separated organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford compound 5a. LCMS (mlz): 251.05(M+1).

References: [1]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000674.

17
[ 360576-01-8 ]
[ 411235-57-9 ]
methyl 6-cyclopropylbenzo[b]thiophene-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In toluene; at 20℃; for 7.5h;Inert atmosphere; Reflux;	To a solution of compound B-110 (2.7 g, 10 mmol) and cyclopropylboronic acid (0.73 g, 10 mmol) in anhydrous toluene (50 mL) under N2 was added tetrakis(triphenylphosphine)palladium(0) (0.54 g, 0.47 mmol), followed by a solution of potassium phosphate (3.2 g, 15 mmol) in water (5 mL). The solution was stirred at room temperature for 0.5 hour before being heated to reflux for 7 hours. On completion, the mixture was cooled to room temperature and filtered. The filtrate was concentrated and purified by silica gel chromatography [petroleum ether: ethyl acetate = 60: 1] to give compound B-lll (1.8 g, 70% yield) as a white solid. LCMS: (ES+) m/z (M+H)+ = 233.0.

References: [1]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00287-00288.

18
[ 957207-58-8 ]
[ 411235-57-9 ]
methyl 4-cyclopropyl-2-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 20 - 110℃; for 7.0h;Inert atmosphere;	To a solution of <strong>[957207-58-8]methyl 4-bromo-2-(trifluoromethyl)benzoate</strong> (537 mg, 1.67 mmol) in 13 mL of toluene was added at room temperature cyclopropylboronic acid (220 mg, 2.56 mmol), K3PO4 (641 mg, 3.02 mmol), water (0.4 mL) and Pd(Ph3)4 (193 mg, 0.167 mmol) and the resulting mixture was degassed for 10 minutes with a stream of N2. The reaction mixture was stirred at 110 C for 7 hours. Water was added and product was extracted with ethyl acetate (three times). The collected organic layers were dried over Na2SO4, filtered and evaporated in high vacuum to yield methyl 4-cyclopropyl-2-(trifluoromethyl)benzoate (crude, 802 mg) as agrey solid. MS found for C12H11F3O2 as (M+H)+ 245.0.

References: [1]Patent: WO2016/196776,2016,A2 .Location in patent: Paragraph 00894.

19
[ 39795-60-3 ]
[ 411235-57-9 ]
C₁₄H₁₃N [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 9152 - 9155.

20
[ 63927-22-0 ]
[ 411235-57-9 ]
8-cyclopropylisoquinoline [ No CAS ]

References: [1]Journal of the American Chemical Society,2017,vol. 139,p. 9767 - 9770.

21
[ 1046816-75-4 ]
[ 411235-57-9 ]
C₈H₁₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 3h;	General procedure: To a solution of and halide in the indicated solvent is added boronic acid or ester, carbonate base, and palladium catalyst at room temperature. After stirring at 100 °C overnight, the mixture is cooled and concentrated.Following Procedure B using 5 (200 mg, I .4 mmoi), cyciopropyihoronic acid(356 rng, 4.15 mmol), sodium carbonate (440 rng, 4.15 rnrnoi), dioxane (10 rnL), water (1rnL), and Pd(PPh3)4 (80 rng, 0.07 mrnoi), react at 10() °C for 3 hours and then purify withsilica gel column chromatography (EA:PE 1:10 to 10:1) to give 64 as a white solid (19 mg,9percent yield). (MS: [M+Hj1 151.1)

References: [1]Patent: WO2017/176812,2017,A1 .Location in patent: Paragraph 0215; 0296.

22
[ 74204-00-5 ]
[ 411235-57-9 ]
3-cyclopropyl-5-methylphenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36.6%	With potassium phosphate; palladium diacetate; tricyclohexylphosphine; In water; toluene; at 100℃;	To a solution of <strong>[74204-00-5]3-bromo-5-methylphenol</strong> (500 mg, 2.67 mmol), cyclopropylboronic acid (344 mg, 4.01 mmol), (3884) tricyclohexylphosphine (150 mg, 0.53 mmol) and potassium (3885) phosphate (1702 mg,. 8..02 mmol) in toluene .(10 mL) /water (2.00 mL) was added Pd(OAc)2 (60.0 mg, 0.27 mmol) at room temperature. The mixture was stirred at 100 °C under Ar overnight. The mixture was quenched with water and extracted with EtOAc. The organic layer was separated, washed with brine, dried over (3886) MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 2percent - 30percent EtOAc in hexane) to give the title compound (144 mg, 0.972 mmol, (3887) 36.3percent) as a pale orange oil. (3888) 1H NMR (300 MHz, CDC13) 5:0.62-0.70 (2H, m) , 0.86-0.97 (2H, m) , 1.74-1.87 (1H, m) , 2.26 (3H, s) , 4.57 (1H, s), 6.33 (1H, s) , 6.43 (1H, s) , 6.49 (1H, s) .

References: [1]Patent: WO2018/30550,2018,A1 .Location in patent: Paragraph 0727.

23
[ 1298031-94-3 ]
[ 411235-57-9 ]
6-chloro-8-cyclopropyl-2-methylimidazo[1,2-b]pyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 90℃; for 48h;Inert atmosphere;	A mixture of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol), cyclopropylboronic acid (843 mg, 9.8 mmol), Pd(dppf)Cl2 (359 mg, 0.49 mmol) and Na2C03 (1.56 g, 14.7 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was stirred at 90 C under N2 for 48 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6-chloro-8-cyclopropyl-2- methylimidazo[l,2-b]pyridazine (405 mg, 40%). MS m/z 208.0, 210.0 [M+H]+.

References: [1]Patent: WO2018/226622,2018,A1 .Location in patent: Page/Page column 89; 185.

24
[ 116632-23-6 ]
[ 411235-57-9 ]
3-cyclopropyl-5-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium phosphate; palladium diacetate; triphenylphosphine; In water; toluene; at 100℃; for 16h;	3.0 g (13.76 mmol) of <strong>[116632-23-6]3-bromo-5-nitrophenol</strong> prepared in Step 213 2), 3.54 g (41.28 mmol) of 6 cyclopropylboronic acid, 8.8 g (41.28 mmol) of 7 potassium phosphate, 310 mg (1.38 mmol) of 8 palladium(II) acetate, and 1.1 g (4.13 mmol) of 9 triphenylphosphine were dissolved in a mixture of 30 mL of 10 toluene and 15 mL of 11 water, followed by stirring under reflux at a temperature of 100° C. for 16 hours. Once the reaction was complete, the mixture was cooled to room temperature, and the mixture was filtered using a celite filter. The resultant was washed with chloroform. An organic layer was separated therefrom, washed with water 2 times, and dried using anhydrous 201 sodium sulfate, followed by removal of a solvent under reduced pressure. The obtained residue was purified using MPLC (chloroform:methanol=20:1 (v/v)), and the resulting solution was concentrated under reduced pressure to thereby obtain 1.52 g of a desired compound at a yield of 62percent. (0391) 1H-NMR (300 MHz, DMSO-d6): delta 10.32 (s, 1H), 7.34 (s, 1H), 7.29 (s, 1H), 6.86 (s, 1H), 1.99 (m, 1H), 0.98 (m, 2H), 0.70 (m, 2H).

References: [1]Patent: US2019/31643,2019,A1 .Location in patent: Paragraph 0389-0391.

25
[ 22300-52-3 ]
[ 411235-57-9 ]
4,5-dibromo-2-cyclopropyl-2H-1,2,3-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2-methylfuran; [2,2]bipyridinyl; copper diacetate; sodium carbonate; In 1,2-dichloro-ethane; at 80℃;	To a 20-L round- bottom flask were placed <strong>[22300-52-3]4,5-dibromo-2H-1,2,3-triazole</strong> (500 g, 2.20 mol), DCE (5 L), 2-methylfuran (5 L), cyclopropylboronic acid (379 g, 4.41 mol), Cu(OAc)2(401 g, 2.20 mol), 2,2-bipyridyl (344 g, 2.21 mol) and sodium carbonate (467 g,4.41 mol). The mixture was stirred overnight at 80 °C. After the reaction was cooled to room temperature, the mixture was filtered. The filtrate was concentrated under vacuum, dissolved in 5 L of EtOAc, washed with 2x1 L of 1 N hydrogen chloride and then with lxi L of brine, dried over sodium sulfate(Na2SO4), and concentrated under vacuum to afford the product.

References: [1]Patent: WO2019/75291,2019,A1 .Location in patent: Page/Page column 116; 266; 267.

26
[ 220939-72-0 ]
[ 411235-57-9 ]
4-chloro-3-cyclopropylfuro[3,2-c]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 3753 - 3772.

27
[ 246847-98-3 ]
[ 411235-57-9 ]
5-cyclopropyl-3-fluoropyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate;	Example 171 Synthesis of 5-cyclopropyl-3-fluoropyridin-2-amine. A mixture of <strong>[246847-98-3]5-chloro-3-fluoropyridin-2-amine</strong> (2 g, 13.65 mmol), cyclopropylboronic acid (1.76 g, 20.47 mmol), Pd(OAc)2 (306 mg, 1.365 mmol), SPhos (1.12 g, 2.73 mmol) and K3PO4 (10.14 g, 47.78 mmol) in toluene (40 mL) and H2O (10 mL) was stirred at 90 C. for 16 h under N2. The reaction mixture was filtered and washed with EtOAc. The combined filtrate was washed with H2O (100 mL) and brine (100 mL), dried over Na2SO4, concentrated and purified by silica gel chromatography (EA/PE=1/2) to give 5-cyclopropyl-3-fluoropyridin-2-amine (2.2 g, yield: 100%) as a yellow syrup. ESI-MS [M+H]+: 153.2.

References: [1]Patent: US2019/284182,2019,A1 .

28
[ 21344-24-1 ]
[ 411235-57-9 ]
5-cyclopropylthieno[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate;	Example 189 Synthesis of 5-cyclopropylthieno[2,3-b]pyridine. To a solution of <strong>[21344-24-1]5-bromothieno[2,3-b]pyridine</strong> (2 g, 9.34 mmol) in dioxane/H2O (100 mL/100 mL) was added cyclopropylboronic acid (1.605 g, 18.7 mmol), Pd(OAc)2 (210 mg, 0.934 mmol), PCy3 (524 mg, 1.87 mmol) and K3PO4 (5.949 g, 28 mmol). The reaction mixture was stirred at 100 C. for 14 h under nitrogen. The mixture was concentrated in vacuo. Water (100 mL) was added and the mixture was extracted with EtOAc (100 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to give the crude product, which was purified by silica gel chromatography (PE/EtOAc=30/1) to give the 5-cyclopropylthieno[2,3-b]pyridine as a yellow oil (1.067 g, yield: 65%). ESI-MS [M+H]+: 175.9.

References: [1]Patent: US2019/284182,2019,A1 .

29
[ 944401-65-4 ]
[ 411235-57-9 ]
5-cyclopropyl-6-fluoropyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate;	Example 142 Synthesis of 5-cyclopropyl-6-fluoropyridin-2-amine. To a solution of <strong>[944401-65-4]5-bromo-6-fluoropyridin-2-amine</strong> (40 g, 209 mmol) in dioxane/H2O (400 mL/40 mL) was added cyclopropylboronic acid (36 g, 418 mmol), Pd(OAc)2 (4.7 g, 21 mmol), PCy3 (11.75 g, 42 mmol) and K3PO4 (133 g, 628 mmol), then the mixture was stirred at 100 C. for 16 h. The mixture was treated with H2O (100 mL) and extracted with EtOAc (300 mL*3). The organic layers were concentrated to give the crude product, which was purified by flash silica gel chromatography (PE/EA=2/1) to give 5-cyclopropyl-6-fluoropyridin-2-amine (26 g, yield: 81%) as a white solid. ESI-MS [M+H]+: 153.1.
	With palladium diacetate;	Example 144 Synthesis of 5-cyclopropyl-6-fluoropyridin-2-amine. To a solution of <strong>[944401-65-4]5-bromo-6-fluoropyridin-2-amine</strong> (40 g, 209 mmol) in dioxane/H2O (400 mL/40 mL) was added cyclopropylboronic acid (36 g, 418 mmol), Pd(OAc)2 (4.7 g, 21 mmol), PCy3 (11.75 g, 42 mmol) and K3PO4 (133 g, 628 mmol), then the mixture was stirred at 100 C. for 16 h. The mixture was treated with H2O (100 mL) and extracted with EtOAc (300 mL*3). The organic layers were concentrated to give the crude product, which was purified by flash silica gel chromatography (PE/EA=2/1) to give 5-cyclopropyl-6-fluoropyridin-2-amine (26 g, yield: 81%) as a white solid. ESI-MS [M+H]+: 153.1.
	With palladium diacetate;	Synthesis of 5-cyclopropyl-6-fluoropyridin-2-amine. A solution of <strong>[944401-65-4]5-bromo-6-fluoropyridin-2-amine</strong> (3.0 g, 15.8 mmol), cyclopropylboronic acid (2.04 mg, 23.7 mmol), Pd(OAc)2 (354 mg, 1.58 mmol), PCy3 (886.2 mg, 3.16 mmol) and K3PO4(6.7 g, 31.6 mmol) in dioxane/H2O (30 mL/3 mL) was stirred at 100 C. for 16 h. Then the reaction mixture was diluted with H2O (50 mL) and extracted with EtOAc (100 mL*3). The combined organic layers were dried over Na2SO4 and concentrated to give the desired compound 5-cyclopropyl-6-fluoropyridin-2-amine (yellow oil, 2.2 g). ESI-MS [M+H]+: 153.2.

References: [1]Patent: US2019/284182,2019,A1 .
[2]Patent: US2019/284182,2019,A1 .
[3]Patent: US2019/284182,2019,A1 .

30
[ 433226-06-3 ]
[ 411235-57-9 ]
ethyl 2-amino-5-cyclopropylnicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate;	Synthesis of ethyl 2-amino-5-cyclopropylnicotinate. The mixture of <strong>[433226-06-3]ethyl 2-amino-5-bromonicotinate</strong> (14.7 g, 60.18 mmol), cyclopropylboronic acid (7.75 g, 90.27 mmol), Pd(OAc)2 (1.35 g, 6.018 mmol), SPhos (4.94 g, 12.04 mmol) and K3PO4 (44.7 g, 210.58 mmol) in a mixture of toluene (200 mL) and H2O (40 mL) was stirred at 100 C. for 16 h. The reaction mixture was filtered through celite and the filtrate was washed with EA (100 mL) and concentrated. The crude product was purified by silica gel chromatography (EA/PE=1/5) to give ethyl 2-amino-5-cyclopropylnicotinate (6.0 g, yield: 48%) as a yellow solid. ESI-MS [M+H]+: 207.1.

References: [1]Patent: US2019/284182,2019,A1 .

31
[ 433226-06-3 ]
[ 411235-57-9 ]
ethyl 2-amino-5-cyclopropylnicotinate [ No CAS ]
ethyl 2-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridine-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium diacetate;	A mixture <strong>[433226-06-3]ethyl 2-amino-5-bromonicotinate</strong> (700 mg, 2.85 mmol), cyclopropylboronic acid (728 mg, 8.5 mmol), Pd(OAc)2 (140 mg, 0.05 mmol), K3PO4 (3 g, 14.2 mmol) and PCy3 (0.3 g, 1.14 mmol) in dioxance/H2O (50 mL/5 mL) was stirred at 95 C. for 12 h in N2. The resulting mixture was quenched with H2O (40 mL), extracted with EtOAc (50 mL*3). The combined organic layers were washed with brine, dried with Na2SO4 and concentrated in vacuo to give the crude, which was purified with silica gel chromatography with PE/EA (1/1) to give ethyl 2-amino-5-cyclopropylnicotinate (500 mg, 86% yield) as a white solid. ESI-MS [M+H]+: 207.1. Purity: 95%. Synthesis of ethyl 2-(chloromethyl)-6-cyclopropylimidazo[1,2-a]pyridine-8-carboxylate.

References: [1]Patent: US2019/284182,2019,A1 .

32
[ 709652-82-4 ]
[ 411235-57-9 ]
2-amino-5-cyclopropylnicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate;	Example 92 Synthesis of 2-amino-5-cyclopropylnicotinonitrile. To a mixture of <strong>[709652-82-4]2-amino-5-bromonicotinonitrile</strong> (1 g, 5.1 mmol), cyclopropylboronic acid (647 mg, 7.6 mmol) and K3PO4 (3.78 g, 17.85 mmol) in toluene/H2O (20 mL/2 mL) was added Pd(OAc)2 (114 mg, 0.51 mmol) and SPhos (209 mg, 0.51 mmol). The mixture was stirred at 95 C. for 16 h. The reaction was cooled to RT and the reaction residue was filtered. The filtrate was concentrated to give the crude product which was purified by silica gel chromatography (EA/PE=4/1) to give 2-amino-5-cyclopropylnicotinonitrile (570 mg, yield: 71%) as a yellow solid. ESI-MS [M+H]+: 160.1.

References: [1]Patent: US2019/284182,2019,A1 .

33
[ 20265-35-4 ]
[ 411235-57-9 ]
3-cyclopropyl-2-methoxypyridine [ No CAS ]

References: [1]Chemical Communications,2019,vol. 55,p. 9287 - 9290.

34
[ 85290-78-4 ]
[ 411235-57-9 ]
ethyl 1-cyclopropyl-3-methyl-1H-pyrazole-4-carboxylate [ No CAS ]
ethyl 1-cyclopropyl-5-methyl-1H-pyrazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%; 15%	With [2,2]bipyridinyl; copper diacetate; potassium carbonate; In 1,2-dichloro-ethane; at 20℃; for 120h;Inert atmosphere;	To a solution of <strong>[85290-78-4]ethyl 3-methyl-1H-pyrazole-4-carboxylate</strong> (1.55 g, 10.1 mmol) in 1,2-dichloroethane (60 mL) was added cyclopropylboronic acid (1.73 g, 20.1 mmol), copper(II) acetate (3.65 g, 20.1 mmol), potassium carbonate (2.78 g, 20.1 mmol), and 2,2?-bipyridine (3.14 g, 20.1 mmol). The reaction mixture was stirred at room temperature for 5 d. To reaction mixture was diluted with water (100 mL) and extracted with chloroform (2×60 mL). The combined organic layers were washed with brine (1×10 mL), dried over magnesium sulfate, filtered and evaporated. The residue was purified by gradient silica gel column chromatography eluting with n-heptane-ethyl acetate (20:1-1:1) to give a 60:40 mixture of the title compounds (290 mg, 1.493 mmol, 15%) as a colorless liquid. Ethyl 1-cyclopropyl-5-methyl-pyrazole-4-carboxylate: MS (ESI): mass calcd. for C10H14N2O2, 194.1; m/z found, 195.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6) delta 7.69 (s, 1H), 4.20 (q, J=6.8 Hz, 2H), 3.64-3.48 (m, 1H), 2.57 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 1.13-1.03 (m, 4H). Fractions from the same column were collected and purified by silica gel column chromatography eluting with n-heptane-ethyl acetate (100:1-1:1) to give pure ethyl 2-cyclopropyl-5-methyl-pyrazole-4-carboxylate (90 mg, 0.463 mmol, 5%) as a colorless liquid. MS (ESI): mass calcd. for C10H14N2O2, 194.1; m/z found, 195.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.21 (s, 1H), 4.18 (q, J=7.1 Hz, 2H), 3.74-3.66 (m, 1H), 2.30 (s, 3H), 1.25 (t, J=7.1 Hz, 3H), 1.09-1.01 (m, 2H), 0.96-0.90 (m, 2H).

References: [1]Patent: US2020/102311,2020,A1 .Location in patent: Paragraph 0410; 0663-0664.

35
[ 85290-78-4 ]
[ 411235-57-9 ]
1-cyclopropyl-5-methyl-1H-pyrazole-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%		To a solution of <strong>[85290-78-4]ethyl 3-methyl-1H-pyrazole-4-carboxylate</strong> (1.55 g, 10.1 mmol) in 1,2-dichloroethane (60 mL) was added cyclopropylboronic acid (1.73 g, 20.1 mmol), copper(II) acetate (3.65 g, 20.1 mmol), potassium carbonate (2.78 g, 20.1 mmol), and 2,2?-bipyridine (3.14 g, 20.1 mmol). The reaction mixture was stirred at room temperature for 5 d. To reaction mixture was diluted with water (100 mL) and extracted with chloroform (2×60 mL). The combined organic layers were washed with brine (1×10 mL), dried over magnesium sulfate, filtered and evaporated. The residue was purified by gradient silica gel column chromatography eluting with n-heptane-ethyl acetate (20:1-1:1) to give a 60:40 mixture of the title compounds (290 mg, 1.493 mmol, 15%) as a colorless liquid. Ethyl 1-cyclopropyl-5-methyl-pyrazole-4-carboxylate: MS (ESI): mass calcd. for C10H14N2O2, 194.1; m/z found, 195.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6) delta 7.69 (s, 1H), 4.20 (q, J=6.8 Hz, 2H), 3.64-3.48 (m, 1H), 2.57 (s, 3H), 1.26 (t, J=7.1 Hz, 3H), 1.13-1.03 (m, 4H). Fractions from the same column were collected and purified by silica gel column chromatography eluting with n-heptane-ethyl acetate (100:1-1:1) to give pure ethyl 2-cyclopropyl-5-methyl-pyrazole-4-carboxylate (90 mg, 0.463 mmol, 5%) as a colorless liquid. MS (ESI): mass calcd. for C10H14N2O2, 194.1; m/z found, 195.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 8.21 (s, 1H), 4.18 (q, J=7.1 Hz, 2H), 3.74-3.66 (m, 1H), 2.30 (s, 3H), 1.25 (t, J=7.1 Hz, 3H), 1.09-1.01 (m, 2H), 0.96-0.90 (m, 2H).Step B: 1-Cyclopropyl-5-methyl-pyrazole-4-carboxylic Acid (0665) To a mixture of ethyl 1-cyclopropyl-5-methyl-pyrazole-4-carboxylate and ethyl 2-cyclopropyl-5-methyl-pyrazole-4-carboxylate (260 mg, 1.34 mmol) in water (1.5 mL) and 1,4-dioxane (1.5 mL) was added sodium hydroxide (120 mg, 3 mmol). The reaction mixture was stirred at 80 C. at 18 h. The reaction mixture was evaporated. The residue was taken up in water (2 mL) and acidified to pH 4 with 1 M hydrochloric acid. The precipitate was collected to afford the title compound (35 mg, 0.211 mmol, 16%) as a white powder. MS (ESI): mass calcd. for C8H10N2O2, 166.1; m/z found, 167.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 12.19 (br s, 1H), 7.65 (s, 1H), 3.59-3.50 (m, 1H), 2.55 (s, 3H), 1.08-0.98 (m, 4H). Structure confirmed by NOESY.

References: [1]Patent: US2020/102311,2020,A1 .Location in patent: Paragraph 0410; 0662; 0665.

Historical Records

Technical Information

• Halogenation • Heat of Combustion • Reactions of Amines

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Code	Phrase
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P378
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Physical hazards
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H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
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H312	Harmful in contact with skin
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H332	Harmful if inhaled
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 411235-57-9

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CAS No.: 411235-57-9

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Product Details of Cyclopropylboronic acid

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Application In Synthesis of Cyclopropylboronic acid

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

[ 411235-57-9 ] Synthesis Path-Downstream 1~35

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