[ CAS No. 108763-47-9 ] {[proInfo.proName]}

Name: 108763-47-9|Methyl benzofuran-5-carboxylate|97%
Brand: Ambeed
SKU: A572921
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Quality Control of [ 108763-47-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 108763-47-9 ]

CAS No. :	108763-47-9	MDL No. :	MFCD06204199
Formula :	C₁₀H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XDRBAVJWSHNLQN-UHFFFAOYSA-N
M.W :	176.17	Pubchem ID :	12674941
Synonyms :

Calculated chemistry of [ 108763-47-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.1
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.49
TPSA :	39.44 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	3.04
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	1.38
Log Po/w (SILICOS-IT) :	2.23
Consensus Log Po/w :	2.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.23
Solubility :	0.104 mg/ml ; 0.000592 mol/l
Class :	Soluble
Log S (Ali) :	-3.53
Solubility :	0.0515 mg/ml ; 0.000292 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.36
Solubility :	0.0769 mg/ml ; 0.000437 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.98

Safety of [ 108763-47-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 108763-47-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 108763-47-9 ]
Downstream synthetic route of [ 108763-47-9 ]

[ 108763-47-9 ] Synthesis Path-Upstream 1~2

1
[ 108763-47-9 ]
[ 90721-27-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide In methanol; water at 65℃; for 4 h;	A stirred mixture of methyl benzofuran-5-carboxylate (1.3 g, 7.38 mmol) in MeOH (51 mL) and sodium hydroxide (41 mL of a 5percent aqueous solution) is heated to 65° C. for 4 h. The mixture is cooled to rt, and MeOH is removed in vacuo. The remaining aqueous layer is extracted with CH2Cl2. The CH2Cl2 layer is discarded, and the aqueous layer is acidified to pH=1 with concentrated hydrochloric acid. The aqueous layer is extracted with CHCl3. The organic layer is washed with water, dried (MgSO4), filtered and concentrated in vacuo to afford 1.2 g (98percent) of benzofuran-5-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) δ12.9, 8.30, 8.11, 7.92, 7.69, 7.09.
98%	With sodium hydroxide In methanol at 65℃; for 4 h;	A stirred mixture OF 4 (1. 3 G, 7. 38 MMOL) in methanol (51 mL) and sodium hydroxide (41 mL of a 5 percent aqueous solution) is heated to 65 C for 4 h. The mixture is cooled to room temperature, and the methanol is removed in vacuo. The remaining aqueous layer is extracted with methylene chloride. The methylene chloride layer is discarded, and the aqueous layer is acidified to PH=L with concentrated hydrochloric acid. The aqueous layer is extracted with chloroform. The organic layer is washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 1.2 g (98percent) of BENZOFURAN-5-CARBOXYLIC acid 5 as a white solid: H NMR (400 MHz, DMSO-D6) 8 12.9, 8.30, 8.11, 7.92, 7.69, 7.09.
98%	With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 18 h;	A solution of LiOH (1.13 g, 47.2 mmol) in water (20 mL) was added to a solution of 123 (2.77 g, 15.7 mmol) in THF (40 mL) and MeOH (40 mL) and the solution was stirred at r.t. for 18 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HCl to pH 2. The precipitate was dissolved in EtOAc, the organic fraction was dried and evaporated to give 124 (2.49 g, 98percent). 1H NMR (DMSO-d₆) δ 12.86 (s, 1H), 8.30 (d, J = 1.4 Hz, 1H), 8.10 (d, J = 2.2 Hz, 1H), 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.68 (dt, J = 8.6, 0.7 Hz, 1H), 7.08 (dd, J = 2.2, 0.9 Hz, 1H).

98%	Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 18 h; Stage #2: With hydrogenchloride In water	A solution of LiOH (1.13 g, 47.2 mmol) in water (20 mL) wasadded to a solution of the above ester (2.77 g, 15.7 mmol) in THF(40 mL) and MeOH (40 mL) and the solution was stirred at 20 Cfor 18 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl to pH 2. The precipitate wasdissolved in EtOAc, the organic fraction was dried and evaporatedto give benzofuran-5-carboxylic acid (2.49 g, 98percent). 1H NMR(DMSO d6) d 12.86 (s, 1H), 8.30 (d, J = 1.4 Hz, 1H), 8.10 (d, J = 2.2Hz, 1H), 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.68 (dt, J = 8.6, 0.7 Hz, 1H),7.08 (dd, J = 2.2, 0.9 Hz, 1H).
65%	Stage #1: With water; sodium hydroxide In methanol at 20℃; for 16 h; Stage #2: With hydrogenchloride In water	To a mixture of methyl benzofuran-5-carboxylate (1.0 g, 5.7 mmol) in methanol (10 mL) and water (1 mL) was added sodium hydroxide (0.45 g, 11 mmol). The mixture was stirred at room temperature for 16 hours. On completion, the mixture was adjusted to pH = 5-6 with 4 M hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration and dried in vacuo to give compound B-139 (0.61 g, 65percent yield) as a white solid.

Reference： [1] Patent: US2003/232853, 2003, A1, . Location in patent: Page 37
[2] Patent: WO2004/39815, 2004, A2, . Location in patent: Page 70
[3] Patent: WO2017/155909, 2017, A1, . Location in patent: Paragraph 0182
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105
[6] Patent: WO2016/100184, 2016, A1, . Location in patent: Paragraph 00341-00342
[7] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436

2
[ 501892-56-4 ]
[ 108763-47-9 ]
[ 90721-27-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide In methanol; water at 50℃; for 2 h;	Methyl 4-hydroxy-3-[(trimethylsilyl)ethynyl]benzoate (11 g, 44.5 mmol) is combined with CuI (423 mg, 2.2 mmol) and DIA (7.1 ml, 50 mmol) in MeOH (110 mL) in a flask under nitrogen. The reaction is warmed to 60° C. for 6 h, the volatiles are removed in vacuo, and the brown-green residue is chromatographed over 500 g silica gel (230-400 mesh) eluting with 20percent EtOAc/hexane. Two pools are isolated to provide 3.43 g (31percent) of the early eluting methyl 2-trimethylsilylbenzofuran-5-carboxylate and 2.63 g (33percent) of the later eluting methyl benzofuran-5-carboxylate. The pools are combined in MeOH (130 mL). The solution is treated with 2N NaOH (46.8 ml, 93.6 mmol), is warmed to 50° C., and is stirred for 2 h. The mixture is cooled, the volatiles are removed in vacuo, and the residue is dissolved in water (50 mL). The pH of the mixture is adjusted to 2 with 12N HCl, is diluted with water (40 mL), and the mixture is cooled to 0° C. The off-white solid is collected, washed with water, and is dried to give 6.0 g. The solid is dried in vacuo over P2O5 for 18 h to give 4.6 g (99percent) of benzofuran-5-carboxylic acid as an off-white solid. MS for C9H6O3, (EI) m/z: 162 (M)+.

Reference： [1] Patent: US2003/232853, 2003, A1, . Location in patent: Page 39

[ 108763-47-9 ] Synthesis Path-Downstream 1~69

1
2-[(E)-2-nitroethenyl]furan [ No CAS ]
[ 292638-85-8 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With hydroquinone at 140℃; for 18h;

Reference： [1]Kusurkar, R. S.; Bhosale, D. K. [Synthetic Communications, 1990, vol. 20, # 1, p. 101 - 109]

2
2-[(E)-2-nitroethenyl]furan [ No CAS ]
[ 140-88-5 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
53%	With hydroquinone at 140℃; for 18h; other 2-(β-sustituted vinyl) furanes; other substituted alkenes;

Reference： [1]Kusurkar, R. S.; Bhosale, D. K. [Synthetic Communications, 1990, vol. 20, # 1, p. 101 - 109]

3
[ 108763-47-9 ]
[ 90721-27-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; In methanol; water; at 65℃; for 4h;	A stirred mixture of methyl benzofuran-5-carboxylate (1.3 g, 7.38 mmol) in MeOH (51 mL) and sodium hydroxide (41 mL of a 5% aqueous solution) is heated to 65 C. for 4 h. The mixture is cooled to rt, and MeOH is removed in vacuo. The remaining aqueous layer is extracted with CH2Cl2. The CH2Cl2 layer is discarded, and the aqueous layer is acidified to pH=1 with concentrated hydrochloric acid. The aqueous layer is extracted with CHCl3. The organic layer is washed with water, dried (MgSO4), filtered and concentrated in vacuo to afford 1.2 g (98%) of benzofuran-5-carboxylic acid as a white solid. 1H NMR (400 MHz, DMSO-d6) delta12.9, 8.30, 8.11, 7.92, 7.69, 7.09.
98%	With sodium hydroxide; In methanol; at 65℃; for 4h;	A stirred mixture OF 4 (1. 3 G, 7. 38 MMOL) in methanol (51 mL) and sodium hydroxide (41 mL of a 5 % aqueous solution) is heated to 65 C for 4 h. The mixture is cooled to room temperature, and the methanol is removed in vacuo. The remaining aqueous layer is extracted with methylene chloride. The methylene chloride layer is discarded, and the aqueous layer is acidified to PH=L with concentrated hydrochloric acid. The aqueous layer is extracted with chloroform. The organic layer is washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford 1.2 g (98%) of BENZOFURAN-5-CARBOXYLIC acid 5 as a white solid: H NMR (400 MHz, DMSO-D6) 8 12.9, 8.30, 8.11, 7.92, 7.69, 7.09.
98%	With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 18h;	A solution of LiOH (1.13 g, 47.2 mmol) in water (20 mL) was added to a solution of 123 (2.77 g, 15.7 mmol) in THF (40 mL) and MeOH (40 mL) and the solution was stirred at r.t. for 18 h and then evaporated. The residue was dissolved in water (50 mL) and acidified with cone. HCl to pH 2. The precipitate was dissolved in EtOAc, the organic fraction was dried and evaporated to give 124 (2.49 g, 98%). 1H NMR (DMSO-d6) delta 12.86 (s, 1H), 8.30 (d, J = 1.4 Hz, 1H), 8.10 (d, J = 2.2 Hz, 1H), 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.68 (dt, J = 8.6, 0.7 Hz, 1H), 7.08 (dd, J = 2.2, 0.9 Hz, 1H).

98%		A solution of LiOH (1.13 g, 47.2 mmol) in water (20 mL) wasadded to a solution of the above ester (2.77 g, 15.7 mmol) in THF(40 mL) and MeOH (40 mL) and the solution was stirred at 20 Cfor 18 h and then evaporated. The residue was dissolved in water(50 mL) and acidified with conc. HCl to pH 2. The precipitate wasdissolved in EtOAc, the organic fraction was dried and evaporatedto give benzofuran-5-carboxylic acid (2.49 g, 98%). 1H NMR(DMSO d6) d 12.86 (s, 1H), 8.30 (d, J = 1.4 Hz, 1H), 8.10 (d, J = 2.2Hz, 1H), 7.92 (dd, J = 8.6, 1.8 Hz, 1H), 7.68 (dt, J = 8.6, 0.7 Hz, 1H),7.08 (dd, J = 2.2, 0.9 Hz, 1H).
65%		To a mixture of methyl benzofuran-5-carboxylate (1.0 g, 5.7 mmol) in methanol (10 mL) and water (1 mL) was added sodium hydroxide (0.45 g, 11 mmol). The mixture was stirred at room temperature for 16 hours. On completion, the mixture was adjusted to pH = 5-6 with 4 M hydrochloric acid, resulting in formation of a solid. The solid was collected by filtration and dried in vacuo to give compound B-139 (0.61 g, 65% yield) as a white solid.

Reference： [1]Patent: US2003/232853,2003,A1 .Location in patent: Page 37
[2]Patent: WO2004/39815,2004,A2 .Location in patent: Page 70
[3]Patent: WO2017/155909,2017,A1 .Location in patent: Paragraph 0182
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1797 - 1809
[5]Journal of Medicinal Chemistry,1995,vol. 38,p. 3094 - 3105
[6]Patent: WO2016/100184,2016,A1 .Location in patent: Paragraph 00341-00342
[7]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436

4
methyl 2-hydroxy-2,3-dihydrobenzofuran-5-carboxylate [ No CAS ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With phosphoric acid at 50℃; for 0.0833333h;

Reference： [1]Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105]

5
[ 588702-80-1 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 2h; Reflux;
61%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Heating / reflux;	1 To a stirred solution of methyl 2,3-dihydrobenzofuran-5-carboxylate (4.2 g, 24 mmol) in anhydrous p-dioxane (150 mL) under argon atmosphere is added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (6.42 g, 28 mmol). The mixture is heated to reflux for 24 h, followed by cooling to rt. The reaction mixture is partitioned between ether and ½ saturated aqueous sodium carbonate solution. The organic layer is extracted several times with ½ saturated aqueous sodium carbonate solution. The organic layer is washed with water, dried(MgSO4), filtered, and concentrated in vacuo to give a mixture (92%) of recovered starting material methyl 2,3-dihydrobenzofuran-5-carboxylate and methyl benzofuran-5-carboxylate in a ratio of 1:3. The crude product is purified by preparative HPLC using a Chiralcel OJ column. Elution with heptane-iso-propyl alcohol, (80:20, flow rate=70 mL/min) gives 0.75 g (18%) of methyl 2,3-dihydrobenzofuran-5-carboxylate as a white solid and 2.5 g (61%) of methyl benzofuran-5-carboxylate as a white solid. 1H NMR for methyl benzofuran-5-carboxylate (400 MHz, CDCl3) δ8.40, 8.07, 7.73, 7.57, 6.89, 3.99.
61%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Heating / reflux;	21.4 Example 21; N-[(3S)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzofuran-5-carboxamide-(2E)-but-2-enedioic acid To a stirred solution of 3 (4.2 g, 24 mmol) in anhydrous p-dioxane (150 mL) under argon atmosphere is added 2,3-dichloro-5, 6-dicyano-1, 4-benzoquinone (6.42 g, 28 mmol). The mixture is heated to reflux for 24 h, followed by cooling to room temperature. The reaction mixture is partitioned between ether AND 1/2 saturated aqueous sodium carbonate solution. The organic layer is extracted several times with 1/2 saturated aqueous sodium carbonate solution. The organic layer is washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 4.2 g (92%) of A, MIXTURE (1: 3) of recovered starting material 3 and methyl benzofuran-5-carboxylate 4, respectively. The crude product is purified by preparative HPLC using a CHIRALCEL OJ column. Elution with heptane-iso-propyl alcohol, (80: 20, flow rate = 70 mL/min) gave 0.75 g (18%) of 3 as A white solid and 2. 5 g (61%) of 4 as a white solid. Benzofuran 4 : LH NMR (400 MHz, CELL3)) 8 8. 40, 8.07, 7. 73, 7.57, 6.89, 3.99.

0.75 g	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Heating;
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chlorobenzene at 85℃; for 2h;

Reference： [1]Location in patent: experimental part Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Hayase, Yoji; Kobayashi, Hiromi; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret S.; Snell, Gyorgy P.; Itoh, Fumio [Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 5, p. 2017 - 2029]
[2]Current Patent Assignee: PFIZER INC - US2003/232853, 2003, A1 Location in patent: Page 30
[3]Current Patent Assignee: PFIZER INC - WO2004/39815, 2004, A2 Location in patent: Page 70
[4]Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. [Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436]
[5]Location in patent: experimental part Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Iwashita, Hiroki; Uno, Yumiko; Onishi, Tomohiro; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret P.; Snell, Gyorgy P.; Takizawa, Masayuki; Itoh, Fumio; Kori, Masakuni [Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6270 - 6286]

6
[ 90843-31-5 ]
[ 108763-47-9 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4425 - 4436

7
[ 76429-73-7 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: H₂SO₄ / 24 h / Heating 2: 0.75 g / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 24 h / Heating

Reference： [1]Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. [Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436]

8
[ 108763-47-9 ]
PHA-543613 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. NaOH / methanol / 4 h / 65 °C 2: diisopropylethylamine; O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium*PF₆ / dimethylformamide / 36 h / 20 °C

9
[ 53596-60-4 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) O₃, 2.) (CH₃)2S / 1.) MeOH, -60 deg C, 3.5 h, 2.) MeOH, 30 deg C, 10 min 2: 95 percent / 85percent H₃PO₄ / 0.08 h / 50 °C

Reference： [1]Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105]

10
[ 108763-47-9 ]
[ 56540-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 94 percent / 85percent KOH / ethanol / 2 h / Heating 2: SOCl₂, DMF / Ambient temperature
	Multi-step reaction with 2 steps 1.1: water; sodium hydroxide / methanol / 16 h / 20 °C 1.2: pH 5-6 2.1: thionyl chloride / 2 h / 60 °C

Reference： [1]Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105]
[2]Current Patent Assignee: FORUM PHARMACEUTICALS INC; SIO GENE THERAPIES INC - WO2016/100184, 2016, A1

11
[ 108763-47-9 ]
Benzofuran-5-yl-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 94 percent / 85percent KOH / ethanol / 2 h / Heating 2: SOCl₂, DMF / Ambient temperature 3: EtAlCl₂ / CH₂Cl₂; toluene / -78 - 20 °C

Reference： [1]Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105]

12
[ 108763-47-9 ]
Benzofuran-5-yl-[2-methyl-1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 94 percent / 85percent KOH / ethanol / 2 h / Heating 2: SOCl₂, DMF / Ambient temperature 3: EtAlCl₂ / CH₂Cl₂; toluene / -78 - 20 °C

Reference： [1]Eissenstat, Michael A.; Bell, Malcolm R.; D'Ambra, Thomas E.; Alexander, E. John; Daum, Sol J.; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3094 - 3105]

13
[ 108763-47-9 ]
[ 74-89-5 ]
[ 633701-49-2 ]

Yield	Reaction Conditions	Operation in experiment
		The other compounds of Example 3 were prepared by essentially the same procedure using the corresponding carboxamide and acyl hydrazide. Acetonitrile was used as solvent in the preparation of 3-2. Compound [3-19] was isolated as a byproduct in the synthesis of 3-18. The methyl amides were prepared from their corresponding methyl esters and [METHYLAMINE] using well established protocols. The other amides were conveniently prepared from commercially available carboxylic acids and amines using 1- (dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride as the reagent and published procedures. Preparation of the acyl hydrazides was described in Procedures 3A, 3B, 3C and 3D.

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2003/104207, 2003, A2 Location in patent: Page 54

14
[ 219763-27-6 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With polyphosphoric acid In 1,2-dichloro-ethane for 1h; Heating / reflux;	34.2 5-(Methoxycarbonyl)benzo[b]furan Preparation Example 34-2 5-(Methoxycarbonyl)benzo[b]furan methyl 4-((2,2-dimethoxy)ethoxy)benzoate (10.00 g) and polyphosphoric acid (20.00 g) were refluxed in 1,2-dichloroethane (50 ml) for 1 hr.. After cooling, ice was added, and the separated organic layer was washed with 10% hydrochloric acid.. The mixture was dried over magnesium sulfate, concentrated and purified by column chromatography to give the objective compound (0.86 g). 1H-NMR(CDCl3, δ ppm): 3.94(3H, s), 6.85(1H, dd, J=2.4 and 0.8 Hz), 7.53(1H, d, J=8.6 Hz), 7.69(1H, d, J=2.2 Hz), 8.03(1H, dd, J=8.7 and 1.7 Hz), 8.35(1H, d, J=1.7 Hz)

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US6348474, 2002, B1 Location in patent: Page column 73

15
[ 108763-47-9 ]
[ 501892-83-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 5-(methoxycarbonyl)benzo[b]furan With bromine; sodium hydrogencarbonate In dichloromethane at 20℃; for 2.5h; Stage #2: With potassium carbonate In ethanol Stage #3: With sodium hydroxide In methanol; water at 20℃; for 3h;	21 Methyl benzofuran-5-carboxylate (667 mg, 3.8 mmol) is dissolved in 20 ml CH2Cl2 in a flask under nitrogen. The solution is treated with Br2 (1.2 ml, 22.8 mmol), is layered with 20 ml saturated NaHCO3, and the reaction is stirred gently for 2 h at RT. The reaction is stirred vigorously for 30 min, the layers are separated, and the organic layer is concentrated in vacuo to an amber oil. The residue is dissolved in 30 ml EtOH, the solution is treated with anhydrous K2CO3 (3.15 g, 22.8 mmol), and the reaction is stirred vigorously overnight. The insoluble material is removed by filtration and the filtrate is diluted with 3 ml 3N NaOH and the mixture is stirred 3 h at RT. The mixture is concentrated in vacuo, the residue is dissolved in 10 ml H2O, and the pH of the solution is adjusted to 2 with 10% aqueous HCl. The precipitate is collected, washed with water, and is dried to afford 880 mg (96%) of 3-bromobenzofuran-5-carboxylic acid as an off-white solid. HRMS (FAB) calcd for C9H5BrO3+H: 240.9501, found 240.9505 (M+H)+.
96%	With water; bromine; sodium hydrogencarbonate In dichloromethane at 20℃; for 2.5h;	3 Example 3; N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-bromo-1-benzofuran-5-carboxamide Methyl BENZOFURAN-5-CARBOXYLATE (667 mg, 3.8 mmol) is dissolved in 20 ml CH2C12 in a flask under nitrogen. The solution is treated with bromine (1.2 ml, 22.8 mmol), is layered with 20 ml saturated sodium bicarbonate, and the reaction is stirred gently for 2 h at rt. The reaction is stirred vigorously for 30 min, the layers are separated, and the organic layer is concentrated ION vacuo to an amber oil. The residue is dissolved in 30 ml ETOH, the solution is treated with anhydrous K2C03 (3.15 g, 22.8 MMOL), and the reaction is stirred vigorously overnight. The insoluble material is removed by filtration, the filtrate is diluted with 3 ml 3N NAOH, and the mixture is stirred 3 h at rt. The mixture is concentrated in vacuo, the residue is dissolved in 10 ml water, and the pH of the solution is adjusted to 2 with 10% aqueous HC1. The precipitate is collected, washed with water, and is dried to afford 880 mg (96%) of 3- BROMOBENZOFURAN-5-CARBOXYLIC acid as an off-white solid. HRMS (FAB) calcd for C9H5BRO3 +H: 240.9501, found 240.9505 (M+H) +.

16
[ 108763-47-9 ]
[ 501892-90-6 ]

Reference： [1]Patent: US2003/232853,2003,A1 .Location in patent: Page 46

17
[ 501892-56-4 ]
[ 108763-47-9 ]
[ 90721-27-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydroxide; In methanol; water; at 50℃; for 2h;	Methyl 4-hydroxy-3-[(trimethylsilyl)ethynyl]benzoate (11 g, 44.5 mmol) is combined with CuI (423 mg, 2.2 mmol) and DIA (7.1 ml, 50 mmol) in MeOH (110 mL) in a flask under nitrogen. The reaction is warmed to 60 C. for 6 h, the volatiles are removed in vacuo, and the brown-green residue is chromatographed over 500 g silica gel (230-400 mesh) eluting with 20% EtOAc/hexane. Two pools are isolated to provide 3.43 g (31%) of the early eluting methyl 2-trimethylsilylbenzofuran-5-carboxylate and 2.63 g (33%) of the later eluting methyl benzofuran-5-carboxylate. The pools are combined in MeOH (130 mL). The solution is treated with 2N NaOH (46.8 ml, 93.6 mmol), is warmed to 50 C., and is stirred for 2 h. The mixture is cooled, the volatiles are removed in vacuo, and the residue is dissolved in water (50 mL). The pH of the mixture is adjusted to 2 with 12N HCl, is diluted with water (40 mL), and the mixture is cooled to 0 C. The off-white solid is collected, washed with water, and is dried to give 6.0 g. The solid is dried in vacuo over P2O5 for 18 h to give 4.6 g (99%) of benzofuran-5-carboxylic acid as an off-white solid. MS for C9H6O3, (EI) m/z: 162 (M)+.

Reference： [1]Patent: US2003/232853,2003,A1 .Location in patent: Page 39

18
[ 501892-55-3 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
34%	With copper(l) iodide; 4-(4-(dihexadecylamino)styryl)-N-methylpyridinium iodide In methanol at 60℃; for 6h;	21 Methyl 4-hydroxy-3-[(trimethylsilyl)ethynyl]benzoate (11 g, 44.5 mmol) is combined with DIA (7.1 ml, 50 mmol) and cuprous iodide (423 mg, 2.2 mmol) in 100 ml MeOH in a flask under nitrogen. The reaction is warmed to 60° C. for 6 h, the volatiles are removed in vacuo, and the brown-green residue is chromatographed over 500 g silica gel (230-400 mesh) eluting with 20% EtOAc/hexane. The appropriate fractions are combined and concentrated to give 2.63 g (34%) of methyl benzofuran-5-carboxylate as a pale oil which crystallized on standing. 1H NMR (300 MHz, CDCl3): δ3.95, 6.86, 7.53, 7.70, 8.03, 8.36 ppm.
34%	With copper(l) iodide; diisopropylamine In methanol at 60℃; for 6h;	3 Example 3; N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-3-bromo-1-benzofuran-5-carboxamide Methyl 4-HYDROXY-3- [ (TRIMETHYLSILYL) ethynyl] benzoate (11 g, 44.5 mmol) is combined with diisopropylamine (7.1 ml, 50 mmol) and cuprous iodide (423 mg, 2.2 mmol) in 100 ml MEOH in a flask under nitrogen. The reaction is warmed to 60C for 6 h, the volatiles are removed in vacuo, and the brown-green residue is chromatographed over 500 g silica gel (230-400 mesh) eluting with 20 % ETOAC/HEXANE. The appropriate fractions are combined and concentrated to give 2.63 g (34%) of methyl BENZOFURAN-5-CARBOXYLATE.'H NMR (300 MHz, CDC13) 8 3.96, 6.86, 7.55, 7.70, 8.04, 8.36 ppm.
400 mg	With copper(l) iodide; N-ethyl-N,N-diisopropylamine In methanol at 60℃; for 16h;	1.1f Step 1f: Preparation of methyl benzofuran-5-carboxylate (compound 0206-1): The compound 4-hydroxy-3-(trimethylsilylethynyl)benzoic acid methyl ester (0205-1) (1.5 g, 6.046 mmol, 1.0 equiv)Dissolved in 50 ml of methanol,Copper iodide (57 mg, 0.302 mmol, 0.05 equiv) was then addedAnd diisopropylethylamine (687 mg, 6.79 mmol, 1.1 eq.).The mixture was stirred at 60 °C for 16 hours.reactionAfter completion, the temperature was lowered, the solvent was removed under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 100/1) Purification,The white solid benzofuran-5-carboxylic acid methyl ester was obtained (400 mg, yield: 37.56%).

Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere 2: indium (III) iodide / 1,2-dichloro-ethane / 80 °C / Schlenk technique; Inert atmosphere

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/232853, 2003, A1 Location in patent: Page 46
[2]Current Patent Assignee: PFIZER INC - WO2004/39815, 2004, A2 Location in patent: Page 55
[3]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A Location in patent: Paragraph 0117
[4]Alonso-Marañón, Lorena; Martínez, M. Montserrat; Sarandeses, Luis A.; Gómez-Bengoa, Enrique; Pérez Sestelo, José [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7970 - 7980]

19
[ 67-56-1 ]
[ 501892-55-3 ]
[ 501892-56-4 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 33% 2: 31%	With copper(l) iodide; 4-(4-(dihexadecylamino)styryl)-N-methylpyridinium iodide at 60℃; for 6h;	6 Methyl 4-hydroxy-3-[(trimethylsilyl)ethynyl]benzoate (11 g, 44.5 mmol) is combined with CuI (423 mg, 2.2 mmol) and DIA (7.1 ml, 50 mmol) in MeOH (110 mL) in a flask under nitrogen. The reaction is warmed to 60° C. for 6 h, the volatiles are removed in vacuo, and the brown-green residue is chromatographed over 500 g silica gel (230-400 mesh) eluting with 20% EtOAc/hexane. Two pools are isolated to provide 3.43 g (31%) of the early eluting methyl 2-trimethylsilylbenzofuran-5-carboxylate and 2.63 g (33%) of the later eluting methyl benzofuran-5-carboxylate. The pools are combined in MeOH (130 mL). The solution is treated with 2N NaOH (46.8 ml, 93.6 mmol), is warmed to 50° C., and is stirred for 2 h. The mixture is cooled, the volatiles are removed in vacuo, and the residue is dissolved in water (50 mL). The pH of the mixture is adjusted to 2 with 12N HCl, is diluted with water (40 mL), and the mixture is cooled to 0° C. The off-white solid is collected, washed with water, and is dried to give 6.0 g. The solid is dried in vacuo over P2O5 for 18 h to give 4.6 g (99%) of benzofuran-5-carboxylic acid as an off-white solid. MS for C9H6O3, (EI) m/z: 162 (M)+.

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/232853, 2003, A1 Location in patent: Page 39

20
[ 108763-47-9 ]
[ 501892-83-7 ]
[ 501892-82-6 ]

Yield	Reaction Conditions	Operation in experiment
880 mg (96%)	With bromine; potassium carbonate In ethanol; dichloromethane; water	31 N-[(1S,2R,4R)-7-azabicyclo[2.2.1]hept-2-yl]-3-bromo-1-benzofuran-5-carboxamide hydrochloride EXAMPLE 31 N-[(1S,2R,4R)-7-azabicyclo[2.2.1]hept-2-yl]-3-bromo-1-benzofuran-5-carboxamide hydrochloride Methyl benzofuran-5-carboxylate (667 mg, 3.8 mmol) (described in Example 14) is dissolved in 20 ml CH2Cl2 under nitrogen. The solution is treated with bromine (1.2 ml, 22.8 mmol), is layered with 20 ml saturated NaHCO3, and the reaction is stirred gently for 2 h at RT. The reaction is stirred vigorously for 30 min, the layers are separated, and the organic layer is concentrated in vacuo to an amber oil. The residue is dissolved in 30 ml EtOH, the solution is treated with anhydrous potassium carbonate (3.15 g, 22.8 mmol), and the reaction is stirred vigorously overnight. The insoluble material is removed by filtration and the filtrate is diluted with 3 ml 3N NaOH and the mixture is stirred 3 h at RT. The mixture is concentrated in vacuo, the residue is dissolved in 10 ml water, and the pH of the solution is adjusted to 2 with 10% aqueous HCl. The precipitate is collected, washed with water, and is dried to afford 880 mg (96%) of 3-bromobenzofuran-5-carboxylic acid as an off-white solid. HRMS (FAB) calcd for C9H5BrO3+H: 240.9501, found 240.9505 (M+H)+.

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/105089, 2003, A1

21
[ 108763-47-9 ]
[ 31823-05-9 ]

Yield	Reaction Conditions	Operation in experiment
3.9 g (80%)	With diisobutylaluminium hydride In tetrahydrofuran	7.a (a) (a) 5-Hydroxymethyl-benzofuran (7a) 5.8 g (32.9 mmol) of methyl benzofuran-5-carboxylate are stirred analogously to Example 1 g in 50 ml of tetrahydrofuran with 64.5 ml (98.6 mmol) of DIBAL (1.53 molar) at -70° C. overnight. Yield: 3.9 g (80%); C9 H8 O2 (148.2). NMR (DMSO): δ=4.6 (d, 2H), 5.24 (t, 1H), 6.96 (d, 1H), 7.3 (dd, 1H), 7.58 (d, 1H), 7.62 (s, 1H) and 7.99 (d, 1H) ppm.

Reference： [1]Current Patent Assignee: BAYER AG - US4734407, 1988, A

22
2-[(E)-2-nitroethenyl]furan [ No CAS ]
[ 52745-92-3 ]
5-methoxycarbonyl-4-nitrobenzofuran [ No CAS ]
4,6-dinitro-5-methoxycarbonyl-4,5,6,7-tetrahydrobenzofuran [ No CAS ]
[ 1131538-79-8 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In xylene at 138℃; for 2h; Further byproducts. Title compound not separated from byproducts.;

Reference： [1]Berestovitskaya; Anisimova; Kataeva; Berkova; Jager [Russian Journal of General Chemistry, 2008, vol. 78, # 5, p. 954 - 962]

23
[ 108763-47-9 ]
C₁₀H₈Br₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In dichloromethane at 0 - 20℃; for 1h;

24
[ 108763-47-9 ]
[ 1005205-57-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrazine hydrate Reflux;

25
[ 67-56-1 ]
[ 90721-27-0 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; for 48h;Heating / reflux;	To a stirred solution of i-<strong>[90721-27-0]benzofuran-5-carboxylic acid</strong> (486mg, 3mmol) in methanol (10ml), cone sulfuric acid (1 drop) was added. The reaction mixture was heated under reflux for 48h. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and poured into saturated potassium carbonate solution (50ml). The mixture was extrated with ethyl acetate (3 x 10ml). The organic layers were combined, washed with brine (20ml), dried over sodium sulphate, filtered and evaporated. The residue was purified by SP4 column eluting with ethyl acetate/hexane solvent system to yield 400mg of white solid. LC-MS: (MH+=177)

Reference： [1]Patent: WO2009/71577,2009,A1 .Location in patent: Page/Page column 36

26
[ 1195960-33-8 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) In pyridine at 90℃; for 2h;
42%	With indium (III) iodide In 1,2-dichloro-ethane at 80℃; Schlenk technique; Inert atmosphere; regioselective reaction;

Reference： [1]Varela-Fernandez, Alejandro; Gonzalez-Rodriguez, Carlos; Varela, Jesus A.; Castedo, Luis; Saa, Carlos [Organic Letters, 2009, vol. 11, # 22, p. 5350 - 5353]
[2]Alonso-Marañón, Lorena; Martínez, M. Montserrat; Sarandeses, Luis A.; Gómez-Bengoa, Enrique; Pérez Sestelo, José [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7970 - 7980]

27
[ 108763-47-9 ]
methyl 2,3-dibromo-2,3-dihydro-1-benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In dichloromethane at 0 - 20℃;

Reference： [1]Location in patent: experimental part Saitoh, Morihisa; Kunitomo, Jun; Kimura, Eiji; Iwashita, Hiroki; Uno, Yumiko; Onishi, Tomohiro; Uchiyama, Noriko; Kawamoto, Tomohiro; Tanaka, Toshimasa; Mol, Clifford D.; Dougan, Douglas R.; Textor, Garret P.; Snell, Gyorgy P.; Takizawa, Masayuki; Itoh, Fumio; Kori, Masakuni [Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6270 - 6286]

28
[ 15126-06-4 ]
[ 140-88-5 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro{bis[1-(dicyclohexylphosphanyl); potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 140℃; Inert atmosphere;

Reference： [1]Oberholzer, Miriam; Gerber, Roman; Frech, Christian M. [Advanced Synthesis and Catalysis, 2012, vol. 354, # 4, p. 627 - 641]

29
[ 1942-46-7 ]
[ 108763-47-9 ]
copper(II) dipivaloate [ No CAS ]
methyl (E)-2-(6-(pivaloyloxy)dec-5-en-5-yl)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 2,2',3,3',4,4',5,5',6,6'-Decabromodiphenyl ether In decane; water at 140℃; for 3h; Inert atmosphere; diastereoselective reaction;

Reference： [1]Pham, Manh V.; Cramer, Nicolai [Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14575 - 14579][Angew. Chem., 2014, vol. 126, # 52, p. 14803 - 14807,5]

30
[ 872-05-9 ]
[ 108763-47-9 ]
[ 1451182-86-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis(1,5-cyclooctadiene)nickel⁽⁰⁾; C₂₉H₄₁N₂; sodium t-butanolate In toluene at 50℃; for 21h; Glovebox; Sealed tube;

Reference： [1]Schramm, York; Takeuchi, Makoto; Semba, Kazuhiko; Nakao, Yoshiaki; Hartwig, John F. [Journal of the American Chemical Society, 2015, vol. 137, # 38, p. 12215 - 12218]

31
[ 154357-93-4 ]
[ 108763-47-9 ]
methyl 2-(bromodifluoromethyl)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylhydroperoxide In decane; dichloromethane; acetonitrile at 20℃; for 16h;	General experimental procedure for bromodifluoromethylation of heteroaromatics with BrCF₂SO₂Na General procedure: To a solution of substrate 1 (1.0 mmol, 1 equiv), NaSO2CF2Br (23.4 mg, 2.0 mmol, 2.0 equiv) in CH2Cl2 (7.0 mL) and CH3CN (3.5 mL) at room temperature was slowly added TBHP (5.0-6.0 M in decane, 1.4 mL, 7 equiv). The reaction was then stirred for 16 h. After the reaction was complete, the reaction mixture was concentrated under vacuum and the crude product was purified by column chromatography on silica gel to give the product.

Reference： [1]Zhang, Jin; Xu, Xiu-Hua; Qing, Feng-Ling [Tetrahedron Letters, 2016, vol. 57, # 22, p. 2462 - 2464]

32
[ 108763-47-9 ]
2-chlorobenzofuran-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: water; sodium hydroxide / methanol / 16 h / 20 °C 1.2: pH 5-6 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C 2.2: 2.5 h / 20 °C

Reference： [1]Current Patent Assignee: FORUM PHARMACEUTICALS INC; SIO GENE THERAPIES INC - WO2016/100184, 2016, A1

33
[ 108763-47-9 ]
(R)-N-(1'-azaspiro[cyclopropane-1,2'-bicyclo[2.2.2]octan]-3'-yl)benzofuran-5-carboxamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: water; sodium hydroxide / methanol / 16 h / 20 °C 1.2: pH 5-6 2.1: thionyl chloride / 2 h / 60 °C 3.1: triethylamine / dichloromethane / 2 h / 20 °C

Reference： [1]Current Patent Assignee: FORUM PHARMACEUTICALS INC; SIO GENE THERAPIES INC - WO2016/100184, 2016, A1

34
N-(benzenesulfonyl)-N-[(trifluoromethyl)sulfanyl]benzenesulfonamide [ No CAS ]
[ 108763-47-9 ]
methyl 3-(trifluoromethylthio)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In N,N-dimethyl-formamide at 80℃; for 1h; Schlenk technique; Inert atmosphere;

Reference： [1]Zhang, Panpan; Li, Man; Xue, Xiao-Song; Xu, Chunfa; Zhao, Qunchao; Liu, Yafei; Wang, Haoyang; Guo, Yinlong; Lu, Long; Shen, Qilong [Journal of Organic Chemistry, 2016, vol. 81, # 17, p. 7486 - 7509]

35
[ 90721-27-0 ]
[ 74-88-4 ]
[ 108763-47-9 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 15315 - 15318

36
[ 108763-47-9 ]
C₁₇H₁₆O₃ [ No CAS ]
C₁₇H₁₆O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride / toluene / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; acetonitrile / 4 h / 80 °C / Darkness; Inert atmosphere 2.2: 2 h / 40 °C / Darkness; Inert atmosphere

Reference： [1]Saito, Hayate; Otsuka, Shinya; Nogi, Keisuke; Yorimitsu, Hideki [Journal of the American Chemical Society, 2016, vol. 138, # 47, p. 15315 - 15318]

37
[ 108763-47-9 ]
6-(methoxycabonyl)benz[e]-1,2-oxaborin-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride / toluene / 12 h / 100 °C / Inert atmosphere; Schlenk technique 2: hydrogenchloride; water / toluene

Reference： [1]Saito, Hayate; Otsuka, Shinya; Nogi, Keisuke; Yorimitsu, Hideki [Journal of the American Chemical Society, 2016, vol. 138, # 47, p. 15315 - 15318]

38
[ 108763-47-9 ]
[ 534-17-8 ]
[ 73183-34-3 ]
C₁₆H₂₀BO₅^(1-)*Cs⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride In toluene at 100℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Saito, Hayate; Otsuka, Shinya; Nogi, Keisuke; Yorimitsu, Hideki [Journal of the American Chemical Society, 2016, vol. 138, # 47, p. 15315 - 15318]

39
[ 617-86-7 ]
[ 108763-47-9 ]
methyl 2-(triethylsilyl)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tert-butylethylene; C₂₅H₄₀O₂P₂Ru In neat (no solvent) at 120℃; for 24h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;

Reference： [1]Fang, Huaquan; Guo, Le; Zhang, Yuxuan; Yao, Wubing; Huang, Zheng [Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627]

40
[ 99-76-3 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 24 h / Reflux 2: polyphosphoric acid / toluene / 12 h / Reflux
	Multi-step reaction with 2 steps 1: sodium hydride / DMF (N,N-dimethyl-formamide) / 18 h / 80 °C 2: polyphosphoric acid / 1,2-dichloro-ethane / 1 h / Heating / reflux
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C / Inert atmosphere 1.2: 5 h / 130 °C / Inert atmosphere 2.1: polyphosphoric acid / toluene / 5 h / Reflux; Inert atmosphere

Reference： [1]Fang, Huaquan; Guo, Le; Zhang, Yuxuan; Yao, Wubing; Huang, Zheng [Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627]
[2]Current Patent Assignee: ASTELLAS PHARMA INC. - US6348474, 2002, B1
[3]Xu-Xu, Qing-Feng; Liu, Qiang-Qiang; Zhang, Xiao; You, Shu-Li [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15204 - 15208][Angew. Chem., 2018, vol. 130, # 46, p. 15424 - 15428,5]

41
[ 93749-47-4 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
9%	With polyphosphoric acid In toluene for 5h; Reflux; Inert atmosphere;
	With polyphosphoric acid In toluene for 12h; Reflux;

Reference： [1]Xu-Xu, Qing-Feng; Liu, Qiang-Qiang; Zhang, Xiao; You, Shu-Li [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15204 - 15208][Angew. Chem., 2018, vol. 130, # 46, p. 15424 - 15428,5]
[2]Fang, Huaquan; Guo, Le; Zhang, Yuxuan; Yao, Wubing; Huang, Zheng [Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627]

42
[ 1873-88-7 ]
[ 108763-47-9 ]
methyl 2-(1,1,1,3,5,5,5-heptamethyltrisiloxan-3-yl)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert-butylethylene; C₂₅H₄₀O₂P₂Ru In neat (no solvent) at 120℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;

Reference： [1]Fang, Huaquan; Guo, Le; Zhang, Yuxuan; Yao, Wubing; Huang, Zheng [Organic Letters, 2016, vol. 18, # 21, p. 5624 - 5627]

43
[ 67-56-1 ]
[ 23145-07-5 ]
[ 201230-82-2 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In dimethyl sulfoxide; at 80℃; under 3102.97 Torr; for 18h;	A mixture of <strong>[23145-07-5]5-bromobenzofuran</strong> (4.00 g, 20.3 mmol), DPPP (0.42 g, 1 mmol), triethylamine (6.3 mL, 45 mmol) and Pd(OAc)2 (0.23 g, 1 mmol) in DMSO (30 mL) and MeOH (30 mL) in a Berghof pressure reactor was evacuated then purged three times with carbon monoxide. The mixture was heated to 80 C for 18 h under 60 psi of carbon monoxide pressure, cooled and partitioned between EtOAc and water. Column chromatography with 3 : 1 (0583) hexanes:DCM eluted traces of impurities while elution with DCM gave 123 (2.77 g, 78%). 1H MR (CDC13) δ 8.35 (d, J = 1.4 Hz, 1H), 8.03 (dd, J = 8.7, 1.7 Hz, 1H), 7.69 (d, J =2.2 Hz, 1H), 7.53 (dt, J = 8.7, 0.8 Hz, 1H), 6.84 (dd, J = 2.2, 1.0 Hz, 1H), 3.94 (s, 3H).
78%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In dimethyl sulfoxide; at 80℃; under 3102.97 Torr; for 18h;	4.1.2.4. 1-(Benzofuran-5-yl)-3-(dimethylamino)propan-1-one (classD-5). A mixture of <strong>[23145-07-5]5-bromobenzofuran</strong> (4.00 g, 20.3 mmol), DPPP(0.42 g, 1 mmol), triethylamine (6.3 mL, 45 mmol) and Pd(OAc)2(0.23 g, 1 mmol) in DMSO (30 mL) and MeOH (30 mL) in a Berghofpressure reactor was evacuated then purged three times with carbonmonoxide. The mixture was heated to 80 C for 18 h under 60psi of carbon monoxide pressure, cooled and partitioned betweenEtOAc and water. Column chromatography with 3:1 hexanes:DCM eluted traces of impurities while elution with DCM gavemethyl benzofuran-5-carboxylate (2.77 g, 78%). 1H NMR (CDCl3) d8.35 (d, J = 1.4 Hz, 1H), 8.03 (dd, J = 8.7, 1.7 Hz, 1H), 7.69 (d, J =2.2 Hz, 1H), 7.53 (dt, J = 8.7, 0.8 Hz, 1H), 6.84 (dd, J = 2.2, 1.0 Hz,1H), 3.94 (s, 3H).

Reference： [1]Patent: WO2017/155909,2017,A1 .Location in patent: Paragraph 0181
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1797 - 1809

44
[ 108763-47-9 ]
[ 1207259-19-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C 2.2: 18 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: lithium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C 1.2: pH 2 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C 2.2: 18 h / 20 °C

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC; TB ALLIANCE INC; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT INC - WO2017/155909, 2017, A1
[2]Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809]

45
[ 108763-47-9 ]
1-(benzofuran-5-yl)-3-(dimethylamino)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium hydroxide; water / tetrahydrofuran; methanol / 18 h / 20 °C 2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C 2.2: 18 h / 0 - 20 °C 3.1: tetrahydrofuran / 1 h / 0 °C 3.2: 1 h / 20 °C
	Multi-step reaction with 3 steps 1.1: lithium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C 1.2: pH 2 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: tetrahydrofuran / 1 h / 0 °C 3.2: 1 h / 20 °C

46
[ 108763-47-9 ]
C₃₁H₃₀BrNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C 1.2: pH 2 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: tetrahydrofuran / 1 h / 0 °C 3.2: 1 h / 20 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; cyclohexane / 1.5 h / -78 - -40 °C / Inert atmosphere 4.2: 4 h / -78 °C / Inert atmosphere

Reference： [1]Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1797 - 1809]

47
[ 108763-47-9 ]
C₃₂H₃₀N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: lithium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C 1.2: pH 2 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: tetrahydrofuran / 1 h / 0 °C 3.2: 1 h / 20 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; cyclohexane / 1.5 h / -78 - -40 °C / Inert atmosphere 4.2: 4 h / -78 °C / Inert atmosphere 5.1: zinc; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere; Heating 5.2: Inert atmosphere; Heating

48
[ 108763-47-9 ]
C₃₂H₃₃BrN₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium hydroxide / tetrahydrofuran; water; methanol / 18 h / 20 °C 1.2: pH 2 2.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: tetrahydrofuran / 1 h / 0 °C 3.2: 1 h / 20 °C 4.1: diisopropylamine; n-butyllithium / tetrahydrofuran; cyclohexane / 1.5 h / -78 - -40 °C / Inert atmosphere 4.2: 4 h / -78 °C / Inert atmosphere

49
[ 99-96-7 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium iodide; sodium hydroxide; sodium hypochlorite / methanol / 2 h / 5 - 20 °C 2: hydrogenchloride / 65 °C 3: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran; chloroform / 4 h / 50 °C / Inert atmosphere 4: copper(l) iodide; N-ethyl-N,N-diisopropylamine / methanol / 16 h / 60 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

50
[ 37470-46-5 ]
[ 108763-47-9 ]

Reference： [1]Patent: CN107383024,2017,A

51
[ 15126-06-4 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran; chloroform / 4 h / 50 °C / Inert atmosphere 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine / methanol / 16 h / 60 °C
	Multi-step reaction with 3 steps 1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / Inert atmosphere 3: indium (III) iodide / 1,2-dichloro-ethane / 80 °C / Schlenk technique; Inert atmosphere

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A
[2]Alonso-Marañón, Lorena; Martínez, M. Montserrat; Sarandeses, Luis A.; Gómez-Bengoa, Enrique; Pérez Sestelo, José [Journal of Organic Chemistry, 2018, vol. 83, # 15, p. 7970 - 7980]

52
[ 108763-47-9 ]
1-(benzofuran-5-yl)-3-(5-methoxy-2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

53
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(7-methoxy-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

54
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(7-methoxy-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C 4.1: methanol; sodium tetrahydroborate / 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

55
[ 108763-47-9 ]
1-(benzofuran-5-yl)-3-(5-fluoro-2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

56
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(7-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

57
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(7-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C 4.1: methanol; sodium tetrahydroborate / 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

58
[ 108763-47-9 ]
1-(benzofuran-5-yl)-3-(2-fluoro-6-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

59
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(6-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

60
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(6-fluoro-5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: caesium carbonate / isopropyl alcohol / 16 h / 20 °C 3.1: acetic acid / methanol / 16 h / 90 °C 4.1: ethanol; sodium tetrahydroborate / 1 h / 0 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

61
[ 108763-47-9 ]
(Z)-1-(benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere; Cooling with ice

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

62
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere; Cooling with ice 3.1: acetic acid / methanol / 90 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

63
[ 108763-47-9 ]
1-(benzofuran-5-yl)-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere; Cooling with ice 3.1: acetic acid / methanol / 90 °C 4.1: methanol; sodium tetrahydroborate / 3 h / 20 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

64
[ 108763-47-9 ]
C₂₁H₁₇N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -60 °C / Inert atmosphere 1.2: 4.5 h / -60 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / Inert atmosphere; Cooling with ice 2.2: 20 °C / Inert atmosphere; Cooling with ice 3.1: acetic acid / methanol / 90 °C 4.1: acetic acid; potassium carbonate / water; ethanol / 70 °C

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A

65
[ 108763-47-9 ]
[ 756-79-6 ]
dimethyl (2-(benzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74.2%	Stage #1: dimethyl methane phosphonate With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 0.5h; Inert atmosphere; Stage #2: 5-(methoxycarbonyl)benzo[b]furan In tetrahydrofuran; hexane at -60 - 20℃; for 4.5h; Inert atmosphere;	1.1g Step 1g: dimethyl (2-(benzofuran-5-yl)-2-oxoethyl)phosphonate (Compound 0207- 1) Preparation. In the atmosphere of nitrogen,Dimethyl Methyl Phosphate (211 mg, 1.703 mmol, 1.5 eq.)Dissolved in 10 ml of dry tetrahydrofuran.Dry ice/ethanol cooling to -60°C,n-Butyllithium (0.7 ml, 2.5 mol/l in n-hexane, 1.703 mmol, 1.5 eq) was slowly added dropwise.The mixture was stirred at -60°C for 30 minutes.Compound benzofuran-5-carboxylic acid methyl ester (0206-1) (200 mg, 1.135 mmol, 1.0 equiv) was slowly added dropwiseA solution of tetrahydrofuran (10 ml).The mixture is stirred at -60°CAfter another 0.5 hour, the reaction was warmed to room temperature for 4 hours.After the reaction was completed, quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a colorless oily liquid.(Dimethyl 2-(benzofuran-5-yl)-2-oxoethyl)phosphate (226 mg, yield: 74.2%).

Reference： [1]Current Patent Assignee: GUANGZHOU BEBETTER MEDICINE TECH - CN107383024, 2017, A Location in patent: Paragraph 0118

66
4-(((dibenzylamino)oxy)carbonyl)-N,N-diethylaniline [ No CAS ]
[ 108763-47-9 ]
C₂₄H₂₅NO₃ [ No CAS ]
C₂₄H₂₅NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; (dimethoxy)methylsilane; copper diacetate In neat (no solvent) at 45℃; for 36h; Inert atmosphere; enantioselective reaction;

67
[ 108763-47-9 ]
[ 588702-80-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogen In decalin at 150℃; for 16h;

Reference： [1]Bordet, Alexis; El Sayed, Sami; Hetaba, Walid; Leitner, Walter; Luska, Kylie L.; Weidenthaler, Claudia [ACS Catalysis, 2020, p. 2124 - 2130]

68
[ 23145-07-5 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / toluene / 16 h / 100 °C / Sealed tube; Inert atmosphere 2: toluene / 0.5 h / 45 °C

Reference： [1]Bismuto, Alessandro; Boehm, Philip; Morandi, Bill; Roediger, Sven [Angewandte Chemie - International Edition, 2020, vol. 59, # 41, p. 17887 - 17896][Angew. Chem., 2020, vol. 132, # 41, p. 18043 - 18052,10]

69
[ 67-56-1 ]
[ 56540-70-6 ]
[ 108763-47-9 ]

Yield	Reaction Conditions	Operation in experiment
53.6 mg	In toluene at 45℃; for 0.5h;

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Code	Phrase
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P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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

[ CAS No. 108763-47-9 ] {[proInfo.proName]}

Quality Control of [ 108763-47-9 ]

Related Doc. of [ 108763-47-9 ]

Product Details of [ 108763-47-9 ]

Calculated chemistry of [ 108763-47-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 108763-47-9 ]

Application In Synthesis of [ 108763-47-9 ]

[ 108763-47-9 ] Synthesis Path-Upstream 1~2

[ 108763-47-9 ] Synthesis Path-Downstream 1~69

Related Functional Groups of [ 108763-47-9 ]

Esters

Related Parent Nucleus of [ 108763-47-9 ]

Benzofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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Inquiry

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[ 108763-47-9 ]

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[ 108763-47-9 ]