Name: 188057-49-0|5-Bromo-2-iodopyridin-3-ol|97%
Brand: Ambeed
SKU: A458523
Price: 9.0 USD
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1
[ 188057-49-0 ]
cis-1-propenylboronic acid [ No CAS ]
[ 1073633-64-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In 1,4-dioxane; water at 100℃;	17.b (b) 5-Bromo-2-[(lZ)-l-propen-l-yl]-3-pyridinol; A mixture of 5-bromo-2-iodo-3-pyridinol (11.16 g, 37.2 mmol), c-propenyl boronic acid (3.84 g, 44.7 mmol) and potassium carbonate (3.84 g, 149 mmol) in 1,4- dioxane/water (3:1, 320 ml) was degassed by bubbling nitrogen through before addition of tetrakis(triphenylphoshine)palladium(0) (0.860 g, 0.74 mmol). The mixture was heated at 1000C overnight, and then evaporated. The aqueous residue was filtered under suction, washed through with DMF, and the filtrate was evaporated to approx. half volume. The residue was then used crude in the next step (assumed 100% yield). MS (+ve ion electrospray) m/z 214/216 (MH+).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/128961, 2008, A1 Location in patent: Page/Page column 27; 76

2
[ 74115-13-2 ]
[ 188057-49-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h; Inert atmosphere;	35 Preparative Example 35 5-bromopyridin-3~ol (1.1 g, 6.3 mmol), iodine (1.6 g, 6.3 mmol), Na2C03 (1.4 g, 13.2 g) and 0 (21 mL) were placed into a 100 mL round bottom flask. The mixture was stirred under N2 at 25 °C for 3 h. The mixture was neutralized with 1 M aqueous solution of HCl and extracted with EtOAc (60+40+40 mL). The organic phase was washed with brine (50 mL), dried over MgS04 and filtered. The product was obtained as a brown solid (1.89 g; 100 %). ]H NMR (300 MHz, CDC13) S 8.08 (d, J= 2.1 Hz, 1H), 7.38 (d, J = 2.1 Hz, 1H), 5.39 (s, 1H).
100%	With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 3.25h;	17.a Example 17; 4- {3- [(2,3-Dihydro [1 ,4] dioxino [2,3-c] pyridin-7-ylmethyl)amino] -3,4- dihydro-2H-pyrano[3,2-6]pyridin-7-yl}-6-(methyloxy)pyrido[2,3-6]pyrazin-3(4H)- one fumarate; (a) 5-Bromo-2-iodo-3-pyridinol; 5-Bromo-3-pyridinol (25.1 g, 144 mmol) was suspended in water (500ml), sodium carbonate (45.9 g, 433 mmol) was added and the mixture was stirred until a clear solution formed. Iodine (36.6 g, 144 mmol) was added in portions over 2.75h while stirring at room temp. Iodine dissolved more quickly as the reaction progressed, giving a dark brown solution which gradually turned to pale yellow. The mixture was stirred for another 30 min, and then added gradually to 150ml 2M hydrochloric acid. A white precipitate formed. More acid was added as required to bring the final pH to approximately 7. The solid was filtered off, washed with water and dried (5O0C, vacuum) to give the product (43.16g , 100%). MS (+ve ion electrospray) m/z 300/302 (MH+).
91%	With iodine; Sodium hydrogenocarbonate In water monomer for 4h;	16.1 1. Synthesis of Intermediate 16-2: To a solution of 5-bromopyridin-3-ol (25 g, 144 mmol, 1.0 equiv) in water (500 mL) were added sodium carbonate (45.9 g, 434 mmol, 3.0 equiv) and I2 (36.6 g, 144 mmol, 1.00 equiv) in portions for a period of 3 h. The mixture was stirred for 1 h and brought to pH 7 with hydrogen chloride (2 N). The resulting precipitate was collected and dried to afford 39 g (91%) of 5-bromo-2-iodopyridin-3-ol as a white solid.

87%	With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h;	8.1 Step 1. To a solution of 5-bromopyridin-3-ol (5.0 g, 28.7 mmol) in H20 (300 mL) wasadded Na2CO3 (6.1 g, 57.5 mmol) and 12 (7.3 g, 28.7 mmol). The mixture was stirred at 25°C for 3 hrs. The reaction mixture was extracted with EtOAc and the combined organiclayers were washed with brine, dried over Na2 SO4, filtered and concentrated under reducedpressure. The crude residue was purified by silica gel chromatography to give 5-bromo-2-iodopyridin-3-ol (7.5 g, 87% yield). ‘HNMR (400 IVIHz, Chloroform-cl) ppm 8.09 (s,1H)7.39 (s, 1 H).
86%	Stage #1: 3-hydroxy-5-bromopyridine With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water monomer Inert atmosphere;
81%	With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 6h; Inert atmosphere;	258 5-bromo-2-iodopyridin-3-ol 5-bromo-2-iodopyridin-3-ol To a solution of 5-bromopyridin-3-ol (20.00 g, 114.95 mmol) in water (400 mL) was added sodium carbonate (40.00 g, 377.40 mmol) and iodine (30.00 g, 118.20 mmol) at room temperature. The resulting solution was stirred for 6 h at room temperature. After the reaction was done, the pH value of the reaction mixture was adjusted to 3 with hydrogen chloride solution (2 M). Precipitation happened. The precipitates were collected by filtration and dried in oven under vacuum to yield 5-bromo-2-iodopyridin-3-ol as a yellow solid (28.00 g, 81%). 1H NMR (400 MHz, CD3OD, ppm) δ 7.93 (s, 1H), 7.24 (d, J=2.0 Hz, 1H).
81%	With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 2h;	1 Take 120.00g (0.690mol) of 3-bromo-5-hydroxypyridine, 2.4L of water, and 219.42g (2.070mol) of sodium carbonate in a flask, add 175.13g (0.690mol) of iodine in batches at 25°C, and continue to react for 2 hours,The reaction was monitored by HPLC, and the remaining amount of raw materials was less than 0.5%; the reaction solution was poured into dilute hydrochloric acid, extracted twice with ethyl acetate, the organic phases were combined, and the solvent was distilled off under reduced pressure.210.00 g of crude product (HPLC purity 93%) was obtained, which was recrystallized with acetic acid and petroleum ether, filtered and dried.167.61 g of compound 1 were obtained (yellow solid, yield 81.0%).
75%	With iodine; anhydrous sodium carbonate In water monomer at 25℃; for 3h; Inert atmosphere;	194.1 Step 1: 5-Bromo-2-iodopyridin-3-ol A mixture of 5-bromopyridin-3-ol (10 g, 57.47 mmol), 12 (14.59 g, 57.47 mmol), andNa2CO3 (12.79 g, 120.69 mmol) in H20 (200 mL) was degassed and purged with N2 (3x) andthen the mixture was stirred at 25 °C for 3 hrs under an N2 atmosphere. The reaction mixture was acidified with 1 M HC1 to pH = 5 and extracted with EtOAc (3x). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford the title compound (13 g, 75%) as a brown solid. ‘H NMR (400 MHz, DMSO-d6) ö 11.40 (s, 1 H), 8.01 (d, J=2. 13 Hz,1 H), 7.30 (d, J=2.13 Hz, 1 H). MS-ESI (m/z) calc’d for C5H4BrINO [M+Hf: 299.8, 301.8. Found 299.8, 301.8.
71%	With iodine; anhydrous sodium carbonate In water monomer at 20℃; for 3h; Inert atmosphere;

Reference： [1]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2015/165428, 2015, A1 Location in patent: Page/Page column 67
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2008/128961, 2008, A1 Location in patent: Page/Page column 27; 75-76
[3]Current Patent Assignee: CYTOKINETICS INC - WO2019/144041, 2019, A1 Location in patent: Paragraph 0265
[4]Current Patent Assignee: REVOLUTION MEDICINES INC - WO2018/136264, 2018, A1 Location in patent: Paragraph 00429; 00460
[5]Location in patent: experimental part Bretéché, Anne; Marchand, Pascal; Nourrisson, Marie-Renée; De Nanteuil, Guillaume; Duflos, Muriel [Tetrahedron, 2010, vol. 66, # 25, p. 4490 - 4494]
[6]Current Patent Assignee: MERCK KGAA - US2016/376283, 2016, A1 Location in patent: Paragraph 0964; 0965
[7]Current Patent Assignee: XIAMEN YUNFAN PHARMACEUTICAL - CN113816955, 2021, A Location in patent: Paragraph 0034-0036
[8]Current Patent Assignee: E SCAPE BIO - WO2021/178780, 2021, A1 Location in patent: Page/Page column 492
[9]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

3
[ 188057-49-0 ]
[ 590-17-0 ]
[ 1236062-30-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In acetone at 20℃; for 18h; Inert atmosphere;
90%	With potassium carbonate In acetone at 20℃; Inert atmosphere;

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Location in patent: experimental part Bretéché, Anne; Marchand, Pascal; Nourrisson, Marie-Renée; De Nanteuil, Guillaume; Duflos, Muriel [Tetrahedron, 2010, vol. 66, # 25, p. 4490 - 4494]

4
[ 625-92-3 ]
[ 188057-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; methanol / 2 h / 80 °C / Inert atmosphere; Microwave irradiation 2: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 3: sodium carbonate; iodine / water / 3 h / 20 °C / Inert atmosphere

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

5
[ 50720-12-2 ]
[ 188057-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 48 h / -78 - 20 °C / Inert atmosphere 2: sodium carbonate; iodine / water / 3 h / 20 °C / Inert atmosphere

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

6
[ 188057-49-0 ]
(E)-N'-(2-cyano-6-phenylfuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

7
[ 188057-49-0 ]
(E)-N'-(2-cyano-6-p-tolylfuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

8
[ 188057-49-0 ]
(E)-N'-(2-cyano-6-(4-methoxyphenyl)furo[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

9
[ 188057-49-0 ]
(E)-N'-(6-(3-chlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

10
[ 188057-49-0 ]
(E)-N'-(6-(3,4-dichlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

11
[ 188057-49-0 ]
(E)-N'-(6-(4-chlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

12
[ 188057-49-0 ]
(E)-N'-(6-(2,4-dichlorophenyl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

13
[ 188057-49-0 ]
(E)-N'-(6-(benzo[d][1,3]dioxol-5-yl)-2-cyanofuro[3,2-b]pyridin-3-yl)-N,N-dimethylformimidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

14
[ 188057-49-0 ]
7-phenylpyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

15
[ 188057-49-0 ]
7-(4-methylphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

16
[ 188057-49-0 ]
7-(4-methoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

17
[ 188057-49-0 ]
7-(3-chlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

18
[ 188057-49-0 ]
7-(3,4-dichlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

19
[ 188057-49-0 ]
7-(4-chlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

20
[ 188057-49-0 ]
7-(2,4-dichlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

21
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: neat (no solvent) / 0.5 h / 170 °C / Inert atmosphere; Microwave irradiation; Sealed tube

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

22
[ 188057-49-0 ]
7-bromo-N-(3,4-dimethoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: acetic acid / 0.17 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

23
[ 188057-49-0 ]
3-amino-6-(benzo[d][1,3]dioxol-5-yl)furo[3,2-b]pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

24
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-phenylpyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

25
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(p-tolyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.75 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.75 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

26
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(4-methoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

27
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dimethoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.33 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: acetic acid / 0.17 h / 118 °C / Inert atmosphere; Microwave irradiation 6: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[3]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

28
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(3,4,5-trimethoxyphenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.67 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.67 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

29
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dichlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 2 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 2 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

30
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(4-chlorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 0.67 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 0.67 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

31
[ 188057-49-0 ]
7-(benzo[d][1,3]dioxol-5-yl)-N-(3-chloro-4-fluorophenyl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 2 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 2 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

32
[ 188057-49-0 ]
N,7-bis(benzo[d][1,3]dioxol-5-yl)pyrido[2',3':4,5]furo[3,2-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Inert atmosphere; Microwave irradiation 5: neat (no solvent) / 0.43 h / 90 °C / Inert atmosphere; Microwave irradiation 6: acetic acid / 1.33 h / 118 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 4: neat (no solvent) / 0.42 h / 90 °C / Microwave irradiation; Inert atmosphere 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / N,N-dimethyl-formamide / 1.5 h / 150 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6: acetic acid / 1.33 h / 118 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]
[2]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

33
[ 188057-49-0 ]
[ 1236062-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

34
[ 188057-49-0 ]
[ 1236062-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / acetone / 18 h / 20 °C / Inert atmosphere 2: pyridine / 1 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Deau, Emmanuel; Loidreau, Yvonnick; Marchand, Pascal; Nourrisson, Marie-Renee; Loaec, Nadege; Meijer, Laurent; Levacher, Vincent; Besson, Thierry [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6784 - 6788]

35
[ 188057-49-0 ]
[ 105-56-6 ]
ethyl 2-amino-6-bromofuro[3,2-b]pyridine-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2-Picolinic acid; copper(l) iodide; caesium carbonate In 1,4-dioxane at 20 - 30℃; for 3h;	120.1 Step 1. Ethyl 6-bromo-2-(tert-butoxycarbonylamino)furo[3,2-b]pyridine-3-carboxylate The mixture of 5-bromo-2-iodopyridin-3-ol (3.00 g, 10.0 mmol), ethyl cyanoacetate (2.26 g, 20.0 mmol), copper(I) iodide (343 mg, 1.80 mmol), 2-pyridinecarboxylic acid (443 mg, 3.60 mmol) and Cs2CO3 (11.7 g, 36.0 mmol) in dioxane (66.7 mL) was stirred at room temperature for 3 h. The reaction mixture was then adjusted to pH 8 with 1 M aq. HCl solution. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated to give a cyclization product.

Reference： [1]Current Patent Assignee: INCYTE CORP - US2015/57265, 2015, A1 Location in patent: Paragraph 1420; 1421

36
[ 188057-49-0 ]
3-(benzyloxy)-5-bromo-2-(trifluoromethyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 80 °C
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 80 °C

Reference： [1]Current Patent Assignee: Valline SRL - WO2015/91685, 2015, A1
[2]Current Patent Assignee: Valline SRL - US2015/166549, 2015, A1

37
[ 188057-49-0 ]
(5-(benzyloxy)-6-(trifluoromethyl)pyridin-3-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 90 °C
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 0 - 20 °C 2: copper(l) iodide / N,N-dimethyl-formamide / 80 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 90 °C

Reference： [1]Current Patent Assignee: Valline SRL - WO2015/91685, 2015, A1
[2]Current Patent Assignee: Valline SRL - US2015/166549, 2015, A1

38
[ 188057-49-0 ]
[ 100-51-6 ]
[ 1342906-74-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h;	a Step a. 3-(benzyloxy)-5-bromo-2-iodopyridine (Intermediate G25. 1) To a solution of 5-bromo-2-iodopyridin-3-ol (0.700 g, 2.334 mmol, preparedaccording to Bioorg. Med. Chem. Lett. 2013, 2, 6784) in dry THF (10 ml), previouslycooled to 0 °C, benzyl alcohol (0.728 ml, 7.00 mmol), TRIPHENYLPHOSPHINE (PPh3)(2.095 ml, 7.00 mmol) and DIISOPROPYL AZODICARBOXYLATE (1.287 ml, 6.54mmol) were added. The reaction was stirred for 4 h at room temperature. Solvent wasremoved and The product was purified by Biotage Si 50 g with a gradient of heptane and EtOAc 3 -(benzyloxy)-5 -bromo-2-iodopyridine (Intermediate G25 .1, 835 mg, 2.141 mmol, 92 % yield) as a white foam.UPLC-MS: mi [M+H]+, method 9
92%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h;	G25.a 3-(benzyloxy)-5-bromo-2-iodopyridine (Intermediate G25.1) To a solution of 5-bromo-2-iodopyridin-3-ol (0.700 g, 2.334 mmol, prepared according to Bioorg. Med. Chem. Lett. 2013, 2, 6784, which is incorporated herein by reference in its entirety) in dry THF (10 ml), previously cooled to 0° C., benzyl alcohol (0.728 ml, 7.00 mmol), triphenylphosphine (PPh3) (2.095 ml, 7.00 mmol) and diisopropyl azodicarboxylate (1.287 ml, 6.54 mmol) were added. The reaction was stirred for 4 h at room temperature. Solvent was removed and the product was purified by Biotage Si 50 g with a gradient of heptane and EtOAc 3-(benzyloxy)-5-bromo-2-iodopyridine (Intermediate G25.1, 835 mg, 2.141 mmol, 92% yield) as a white foam.UPLC-MS: min, [M+H]+, method 9

Reference： [1]Current Patent Assignee: Valline SRL - WO2015/91685, 2015, A1 Location in patent: Page/Page column 152; 153
[2]Current Patent Assignee: Valline SRL - US2015/166549, 2015, A1 Location in patent: Paragraph 0938; 0939

39
[ 188057-49-0 ]
[ 1066-54-2 ]
6-bromo-2-(trimethylsilyl)furo[3,2-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 18 - 25℃; for 17h; Inert atmosphere;	Ethynyltrimethylsilane (246 mg, 2.50 mmol) was added to a mixture of copper(I) iodide (31.8 mg, 0.167 mmol), bis(triphenylphosphine)palladium chloride (117 mg, 0.167 mmol) and 5-bromo-2-iodopyridin-3-ol (500 mg, 1.67 mmol) in triethylamine (lOmL) at r.t. under N2. The resulting mixture was stirred at r.t. for 17h. The solvent was then removed under reduced pressure. Purification by FSC (gradient 0-10% EtOAc in petroleum ether) gave the title compound (340 mg, 75 %) as a brown solid. 1H NMR: δ 0.36 (9H, s), 7.41 (1H, d), 8.44 (1H, dd), 8.61 (1H, d). m/z (ES+), [M+H]+ = 272.1.
61%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In 1,4-dioxane at 45℃; for 3h; Inert atmosphere;	36 Preparative Example 36 The product from Preparative Example 35 (1.88 g, 6.27 mmol), 1 ,4-dioxane (12 mL) and TEA (12 mL) were placed into a 100 mL round bottom flask. The mixture was purged with N2, then ethynyltrimethylsilane (1.15 mL, 8.15 mmol), PdCl2(PPh3)2 (132 mg, 0.188 mmol) and Cul (71 mg, 0.376 mmol) were added. The mixture was stirred under N2 at 45 °C for 3 h. The solvent was evaporated and the residue was purified by column chromatography on silica gel (EtOAc/hexane; 1 :15). The product was obtained as an orange solid (1.04 g, 61 %). NMR (500 MHz, CDCI3) δ 8.58 (d, J (d, J= 1.0 Hz, 1H), 0.37 (s, 9H). I3C NMR (126 MHz, CDCI3) δ 170.2, 150.9, 147.1, 146.8, 121.1, 1 17.1, 115.2, -1.9. HRMS (APCI): calcd. for Ci0H12BrNOSi [M+H]+ = 269.9944; found [M+H]+ = 269.9954.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2022/69520, 2022, A1 Location in patent: Page/Page column 35; 55
[2]Current Patent Assignee: MASARYKOVA UNIVERZITA - WO2015/165428, 2015, A1 Location in patent: Page/Page column 67; 68

40
[ 188057-49-0 ]
[ 100-39-0 ]
[ 1342906-74-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3h;	1.2 Step 2. To a solution of 5-bromo-2-iodo-pyridin-3-ol (29 g, 96.7 mmol) in DMF (400 mL) was added K2C03 (20.0 g, 145.05 mmol) and benzyl bromide (18.2 g, 106.37 mmol, 12 mL). The mixture was stirred at 25 °C for 3 hrs. The reaction mixture was diluted with H20 (200 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography to afford 3-benzyloxy-5-bromo-2-iodo- pyridine (33 g, 88 % yield) as a red solid. ‘H NIVIR (400 MHz, Chloroform-cl) ppm 8.10 (s, 1 H) 7.48-7.34 (m, 5 H) 7.15 (s, 1 H) 5.16 (s, 2 H).
86%	With potassium carbonate In acetonitrile at 0 - 20℃; for 5.5h;	16.2 2. Synthesis of Intermediate 16-3: To a solution of 5-bromo-2-iodopyridin-3-ol (39.5 g, 132 mmol, 1.1 equiv) in ACN (600 mL) was added potassium carbonate (54.5 g, 396 mmol, 3.0 equiv) and BnBr (23.6 g, 138 mmol, 1.05 equiv) dropwise with stirring at 0 oC. The mixture was stirred at r.t. for 5.5 h, cooled to 0 oC, and quenched with the dropwise addition of water at 0 oC. The solids were collected by filtration and triturated with 5% EA in PE (100 mL) to afford 44.4 g (86%) of 3-(benzyloxy)-5-bromo-2-iodopyridine as a white solid.

Reference： [1]Current Patent Assignee: REVOLUTION MEDICINES INC - WO2018/136264, 2018, A1 Location in patent: Paragraph 00430
[2]Current Patent Assignee: CYTOKINETICS INC - WO2019/144041, 2019, A1 Location in patent: Paragraph 0266

41
[ 188057-49-0 ]
[ 1073633-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 100 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C 3: dichloro(tricyclohexylphosphino)(benzylidene)(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)ruthenium(III) / toluene / 48 h / 90 °C