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Name: 52428-09-8|4,7-Dimethoxy-2,3-dihydro-1H-inden-1-one|98%
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Product Details of [ 52428-09-8 ]

CAS No. :	52428-09-8	MDL No. :	MFCD00757244
Formula :	C₁₁H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MSGQVFMAKBIPNF-UHFFFAOYSA-N
M.W :	192.21	Pubchem ID :	606012
Synonyms :

Safety of [ 52428-09-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 52428-09-8 ]

* 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 [ 52428-09-8 ]
Downstream synthetic route of [ 52428-09-8 ]

[ 52428-09-8 ] Synthesis Path-Upstream 1~9

1
[ 10538-49-5 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	at 80℃; for 4 h;	A mixture of compound 8-1 (4.68 g.22.3 mmol) and PPA (50.87 g.24.8 mL) was stirred at 80 °C for 4.0 hrs. After the reaction was completed.250 mL of ice water was added to the mixture, and the resulting mixture was extracted with EtOAc (100 mL x 5). The combined organic layers were washed with NaHCCh aqueous solution and brine, dried over anhydrous a^SO.) and concentrated in vacuo. The residue was purified silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound 8-2 as a pale yellow solid (3.0 g.70.0percent). The compound was characterized the following spectroscopic data: MS (ESI. pos.ion) ml:: 193.2 [M+H] and _{v 3} . . .. . , . , . . (s, 3H), 3.00-2.97 (m.2H), 2.68-2.65 (m, 2H).
70%	at 80℃; for 4 h;	A mixture of compound 1-1 (4.68 g, 22.3 mmol) and PPA (50.87 g, 24.8 mL) in a 100 mL of round-bottomedflask was stirred at 80 °C for 4 hours. Then the mixture was poured into ice water (250 mL) and extracted with EtOAc(100 mL x 5). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residuewas purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a pale yellowsolid (3 g, 70percent, HPLC: 92.5percent). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 193.2 [M+H]+; and1H NMR (400 MHz, CDCl3): δ 6.98 (d, J = 8.7 Hz, 1H), 6.73 (d, J = 8.7 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 2.97-3.00(m, 2H), 2.65-2.68 (m, 2H).

Reference： [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057
[2] Patent: WO2014/82379, 2014, A1, . Location in patent: Page/Page column 139; 140; 141
[3] Patent: EP2730572, 2015, B1, . Location in patent: Paragraph 0259; 0261
[4] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915[5] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062
[6] Patent: EP2730572, 2014, A1, . Location in patent: Page/Page column 0261
[7] Patent: EP2730572, 2015, B1, . Location in patent: Page/Page column 0261
[8] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598
[9] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282

2
[ 100126-94-1 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
40 g	With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667 h; Inert atmosphere	Acyl chloride was added to dropwise to a stirred mixture of AlCl₃ (62.6 g, 0.47 mol, 2.0 eq) in anhydrous CH₂Cl₂ (300 ml, 0.8 M) at 0 ^oC using dropping funnel. After 10 minutes, the reaction mixture was poured into 1 M HCl solution at 0 ^oC and extracted with CH₂Cl₂ (200 ml × 3). The organic phase was washed with H₂O and saturated NaHCO₃ solution. The combined organic layer was dried with MgSO₄ and concentrated in vacuo. The product mechanically crushed and stirred in small amount of Et₂O. The product was collected on a glass filter funnel with suction and dried under reduced pressure to give 40.0 g (89percent) of the 5 as a pale orange powder. R_f : 0.32 (EtOAc : Hexane = 1 : 1) ¹H NMR (CDCl₃, 400 MHz) : d 7.00-6.97 (d, J = 8.4 Hz, 1H), 6.74-6.72 (d, J = 8.8 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.00-2.97 (t, J = 5.8 Hz, 2H), 2.68-2.66 (t, J = 5.8 Hz, 2H) ¹³C NMR (CDCl₃, 100 MHz) : d 205.3, 151.8, 150.5, 146.1, 126.3, 116.6, 109.4, 56.1, 55.9, 36.8, 22.4 IR (neat, cm^-1) : 2929, 2832, 1694, 1595, 1496, 1450, 1438, 1401, 1292, 1264, 1233, 1201, 1167, 1068, 1025, 996, 889, 832, 803, 718 LR/MS (m/z) [M+Na⁺] : 215.1

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 1395 - 1400
[2] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598

3
[ 93-02-7 ]
[ 52428-09-8 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1316 - 1327
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915[3] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062
[4] Patent: WO2014/82379, 2014, A1,
[5] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057
[6] Patent: EP2730572, 2014, A1,
[7] Patent: EP2730572, 2015, B1,
[8] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282

4
[ 848610-51-5 ]
[ 52428-09-8 ]

Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1316 - 1327

5
[ 2680-03-7 ]
[ 150-78-7 ]
[ 52428-09-8 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 24, p. 4199 - 4202
[2] Tetrahedron, 1996, vol. 52, # 40, p. 12993 - 13006

6
[ 38489-74-6 ]
[ 52428-09-8 ]

Reference： [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1994, vol. 30, # 8, p. 905 - 915[2] Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062

7
[ 10538-51-9 ]
[ 52428-09-8 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057
[2] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282

8
[ 10538-49-5 ]
[ 71-43-2 ]
[ 52428-09-8 ]

Reference： [1] Journal of the American Chemical Society, 1941, vol. 63, p. 1317,1318
[2] Helvetica Chimica Acta, 1948, vol. 31, p. 536,539

9
[ 150-78-7 ]
[ 52428-09-8 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 24, p. 4199 - 4202

[ 52428-09-8 ] Synthesis Path-Downstream 1~88

1
[ 52428-09-8 ]
[ 65698-22-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With hydrogenchloride In pyridine at 165 - 170℃; for 1.5h;
	With hydrogen bromide
5.1 g	With boron tribromide In dichloromethane at -70℃; for 4h; Inert atmosphere;	8.0 g of 4,7-dimethoxy-1-indanone was added to 80 mL of dichloromethane,Using a dry ice bath under a nitrogen atmosphere,It was cooled and stirred at -70 ° C. There,22.9 g of boron tribromide was added dropwise.After the dropwise addition, the mixture was stirred at -70 ° C. for 4 hours.The reaction solution was returned to room temperature,Pour into ice water,Precipitates were filtered off.Wash the crystals thoroughly with water,And dried under reduced pressure.Recrystallization was carried out with a mixture of ethyl acetate and heptane v / v = 5/1 to obtain 5.1 g of a compound (ex-1).

With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere;

1-Oxo-2,3-dihydro-1H-indene-4,7-diyl diacetate (19) To a stirring solution of 16 (165 mg, 0.858mmol) in anhydrous CH2Cl2 (2 mL) was added boron tribromide (2.6 mL, 2.6 mmol, 1 M solution inCH2Cl2) at -78 °C under an argon atmosphere. The resulting mixture was allowed to warm to roomtemperature. After being stirred for 8 h, the reaction mixture was treated with MeOH. The resultingmixture was stirred for another 1 h at room temperature and then concentrated in vacuo to yield4,7-dihydroxy-2,3-dihydro-1H-inden-1-one as a pale brown solid, which was used for the next reactionwithout further purification. Rf 0.25 (2% MeOH/CHCl3). Mp 168-172 °C. IR ν (neat, cm-1): 3203, 1653,1600, 1476, 1277, 937, 823, 772, 747, 669. 1H-NMR (400 MHz, CD3OD): δ 6.81 (d, J = 8.5 Hz, 1H),6.46 (d, J = 8.5 Hz, 1H), 2.87 (t, J = 5.7 Hz, 2H), 2.54 (t, J = 5.7 Hz, 2H). 13C-NMR (100 MHz, CD3OD):δ 211.0, 151.2, 148.3, 141.9, 124.6, 124.3, 115.1, 37.0, 23.5. LRMS (EI) m/z (relative intensity): 165[M+1]+ (11), 164 [M]+ (100), 136 (17). HRMS (EI, [M]+): calcd for C9H8O3, 164.0473; found, 164.0466

Reference： [1]Al-Hamdany, Raad; Bruce, J. Malcolm; Heatley, Frank; Khalafy, Jabbar [Journal of the Chemical Society. Perkin transactions II, 1985, p. 1395 - 1400]
[2]Hayes; Thomson [Journal of the Chemical Society, 1956, p. 1585,1588]
[3]Current Patent Assignee: CHISSO CORPORATION - JP2018/131421, 2018, A Location in patent: Paragraph 0155; 0156; 0157
[4]Tsukamoto, Hirokazu; Nomura, Yumi; Doi, Takayuki [Heterocycles, 2019, vol. 99, # 1, p. 549 - 565]

2
[ 10538-49-5 ]
[ 71-43-2 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentoxide

Reference： [1]Arnold; Zaugg [Journal of the American Chemical Society, 1941, vol. 63, p. 1317,1318] Posternak; Castro [Helvetica Chimica Acta, 1948, vol. 31, p. 536,539]

3
[ 52428-09-8 ]
[ 69189-19-1 ]
[ 123676-79-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 3067 - 3075
[2]Journal of the American Chemical Society,1989,vol. 111,p. 8979 - 8981

4
[ 52428-09-8 ]
[ 98154-04-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With aluminium trichloride In nitrobenzene at 70℃; for 8h;
24%	With cerium(III) chloride heptahydrate; sodium iodide In N,N-dimethyl-formamide for 120h; Reflux; Inert atmosphere;	7-hydroxy-4-methoxyindan-1-one (7) A mixture of 4,7-dimethoxyindan-1-one (5.0 g, 26.0 mmol, 1.0 eq), cerium chloride hepahydrate (29.1 g, 78.0 mmol, 3.0 eq) and sodium iodide (11.7 g, 78.0 mmol, 3.0 eq) in DMF (130 ml, 0.2 M, Bp 153 oC) was stirred under reflux for 5 days. The reaction mixture was cooled to room temperature and DMF was removed under reduced pressure at 70 oC water bath to leave dark-brown sticky oil material. The reaction mixture was diluted with H2O. The aqueous phase was extracted with CH2Cl2 (500 ml × 3) and washed with H2O. The combined organic layer was dried with MgSO4 and concentrated in vacuo. The residue was purified via flash column chromatography (EtOAc : Hexane = 1 : 2) to provide 7 (1.11 g, 24%, brsm 54%) as a orange powder. Rf : 0.67 (EtOAc : Hexane = 1 : 1) 1H NMR (CDCl3, 400 MHz) : d 8.55 (s, 1H), 7.01-6.99 (d, J = 8.0 Hz, 1H), 6.74-6.72 (d, J = 8.8 Hz, 1H), 3.84 (s, 3H), 3.05-3.03 (t, J = 4.8 Hz, 2H), 2.72-2.70 (t, J = 5.0 Hz, 2H) 13C NMR (CDCl3, 100 MHz) : d 210.3, 150.9, 149.8, 142.5, 123.6, 119.3, 114.0, 56.2, 36.1, 23.0 IR (neat, cm-1) : 3422, 2924, 2841, 1679, 1603, 1495, 1442, 1404, 1318, 1287, 1265, 1231, 1175, 1083, 1041, 992, 969, 945, 899, 836, 732, 715, 671 LR/MS (m/z) [M+H+] : 179.0

Reference： [1]Horaguchi, Takaaki; Tamura, Shigeru; Hiratsuka, Naohiro; Suzuki, Tsuneo [Journal of the Chemical Society. Perkin transactions I, 1985, p. 1001 - 1006]
[2]Kim, Yun Yeong; Pyun, Yu Mi; Jeon, Bo Keun; Lee, Duck-Hyung [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598]

5
[ 52428-09-8 ]
[ 78907-19-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium tetrahydroborate In methanol at 25℃; for 0.5h;
	With sodium tetrahydroborate In ethanol for 12h; Ambient temperature; Yield given;
	With sodium tetrahydroborate In ethanol for 0.5h; Heating;

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]
[2]Braun, Manfred; Bernhard, Carlo [Liebigs Annalen der Chemie, 1985, # 2, p. 435 - 437]
[3]Zhang, Xiang; Thimmaiah, Muralidhara; Fang, Shiyue [Synthetic Communications, 2007, vol. 37, # 11, p. 1873 - 1877]

6
[ 100126-94-1 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With aluminium trichloride In 1,2-dichloro-ethane for 2h; Ambient temperature;
40 g	With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere;	4,7-dimethoxyindan-1-one (5) Acyl chloride was added to dropwise to a stirred mixture of AlCl3 (62.6 g, 0.47 mol, 2.0 eq) in anhydrous CH2Cl2 (300 ml, 0.8 M) at 0 oC using dropping funnel. After 10 minutes, the reaction mixture was poured into 1 M HCl solution at 0 oC and extracted with CH2Cl2 (200 ml × 3). The organic phase was washed with H2O and saturated NaHCO3 solution. The combined organic layer was dried with MgSO4 and concentrated in vacuo. The product mechanically crushed and stirred in small amount of Et2O. The product was collected on a glass filter funnel with suction and dried under reduced pressure to give 40.0 g (89%) of the 5 as a pale orange powder. Rf : 0.32 (EtOAc : Hexane = 1 : 1) 1H NMR (CDCl3, 400 MHz) : d 7.00-6.97 (d, J = 8.4 Hz, 1H), 6.74-6.72 (d, J = 8.8 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 3.00-2.97 (t, J = 5.8 Hz, 2H), 2.68-2.66 (t, J = 5.8 Hz, 2H) 13C NMR (CDCl3, 100 MHz) : d 205.3, 151.8, 150.5, 146.1, 126.3, 116.6, 109.4, 56.1, 55.9, 36.8, 22.4 IR (neat, cm-1) : 2929, 2832, 1694, 1595, 1496, 1450, 1438, 1401, 1292, 1264, 1233, 1201, 1167, 1068, 1025, 996, 889, 832, 803, 718 LR/MS (m/z) [M+Na+] : 215.1

Reference： [1]Al-Hamdany, Raad; Bruce, J. Malcolm; Heatley, Frank; Khalafy, Jabbar [Journal of the Chemical Society. Perkin transactions II, 1985, p. 1395 - 1400]
[2]Kim, Yun Yeong; Pyun, Yu Mi; Jeon, Bo Keun; Lee, Duck-Hyung [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598]

7
[ 52428-09-8 ]
[ 616-38-6 ]
[ 22065-52-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydride In tetrahydrofuran for 14h;
77%	With sodium hydride In toluene; mineral oil at 0 - 120℃; for 18h;

Reference： [1]Khanna; Mitscher [Tetrahedron Letters, 1985, vol. 26, # 6, p. 691 - 694]
[2]Companys, Simon; Peixoto, Philippe A.; Bosset, Cyril; Chassaing, Stefan; Miqueu, Karinne; Sotiropoulos, Jean-Marc; Pouységu, Laurent; Quideau, Stéphane [Chemistry - A European Journal, 2017, vol. 23, # 54, p. 13309 - 13313]

8
[ 52428-09-8 ]
[ 105-58-8 ]
[ 81664-67-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In diethylene glycol dimethyl ether; benzene for 17h; Ambient temperature;

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

9
[ 52428-09-8 ]
[ 127168-82-5 ]
[ 157793-83-4 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1994,vol. 67,p. 3067 - 3075

10
[ 10538-49-5 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 3-(2,5-dimethoxyphenyl)propanoic acid With thionyl chloride; N,N-dimethyl-formamide for 5h; Reflux; Stage #2: With aluminum (III) chloride In dichloromethane at -5℃; for 0.833333h;
70%	With polyphosphoric acid at 80℃; for 4h;	8.2 the preparation of compound 8-2 A mixture of compound 8-1 (4.68 g.22.3 mmol) and PPA (50.87 g.24.8 mL) was stirred at 80 °C for 4.0 hrs. After the reaction was completed.250 mL of ice water was added to the mixture, and the resulting mixture was extracted with EtOAc (100 mL x 5). The combined organic layers were washed with NaHCCh aqueous solution and brine, dried over anhydrous a^SO.) and concentrated in vacuo. The residue was purified silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound 8-2 as a pale yellow solid (3.0 g.70.0%). The compound was characterized the following spectroscopic data: MS (ESI. pos.ion) ml:: 193.2 [M+H] and v 3 . . .. . , . , . . (s, 3H), 3.00-2.97 (m.2H), 2.68-2.65 (m, 2H).
70%	With polyphosphoric acid at 80℃; for 4h;	1.2 the preparation of compound 1-2 A mixture of compound 1-1 (4.68 g, 22.3 mmol) and PPA (50.87 g, 24.8 mL) in a 100 mL of round-bottomedflask was stirred at 80 °C for 4 hours. Then the mixture was poured into ice water (250 mL) and extracted with EtOAc(100 mL x 5). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residuewas purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a pale yellowsolid (3 g, 70%, HPLC: 92.5%). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 193.2 [M+H]+; and1H NMR (400 MHz, CDCl3): δ 6.98 (d, J = 8.7 Hz, 1H), 6.73 (d, J = 8.7 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 2.97-3.00(m, 2H), 2.65-2.68 (m, 2H).

63%	With PPA at 57 - 60℃; for 0.5h;
	With polyphosphoric acid at 80℃; for 4h;	1.2 Step 2) the preparation of compound 1-2 A mixture of compound 1-1 (4.68 g, 22.3 mmol) and PPA (50.87 g, 24.8 mL) in a 100 mL of round-bottomed flask was stirred at 80 °C for 4 hours. Then the mixture was poured into ice water (250 mL) and extracted with EtOAc (100 mL x 5). The combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 3/1) to give the title compound as a pale yellow solid (3 g, 70%, HPLC: 92.5%). The compound was characterized by the following spectroscopic data: MS-ESI: m/z 193.2 [M+H]+; and1H NMR (400 MHz, CDCl3): δ 6.98 (d, J = 8.7 Hz, 1H), 6.73 (d, J = 8.7 Hz, 1H), 3.90 (s, 3H), 3.85 (s, 3H), 2.97-3.00 (m, 2H), 2.65-2.68 (m, 2H).
	Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / 2 h / 23 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
	With methanesulfonic acid; phosphorus pentoxide In dichloromethane at 20℃; for 19h;

Reference： [1]Mejlsoe, Soren L.; Christensen, Jorn B. [Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057]
[2]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/82379, 2014, A1 Location in patent: Page/Page column 139; 140; 141
[3]Current Patent Assignee: ZHANG (inventors); SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - EP2730572, 2015, B1 Location in patent: Paragraph 0259; 0261
[4]Gribkov, A.A.; Borovkov, V.V.; Evstigneeva, R.P.; Sakata, Y. [Chemistry of Heterocyclic Compounds, 1994, vol. 30, # 8, p. 905 - 915][Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062]
[5]Current Patent Assignee: ZHANG (inventors); SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - EP2730572, 2015, B1 Location in patent: Page/Page column 0261
[6]Kim, Yun Yeong; Pyun, Yu Mi; Jeon, Bo Keun; Lee, Duck-Hyung [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 597 - 598]
[7]Kotha, Sambasivarao; Cheekatla, Subba Rao; Mandal, Binita [European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282]

11
[ 52428-09-8 ]
[ 162018-98-6 ]
[ 162019-02-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With PPA at 60℃; for 45h;

Reference： [1]Gribkov, A.A.; Borovkov, V.V.; Evstigneeva, R.P.; Sakata, Y. [Chemistry of Heterocyclic Compounds, 1994, vol. 30, # 8, p. 905 - 915][Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062]

12
[ 52428-09-8 ]
[ 298-12-4 ]
[ 174228-70-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium hydroxide In ethanol; water 1.) room temperature, 1 h, 2.) reflux, 3 h;

Reference： [1]Barlocco, Daniela; Bergomi, Marzia; Menta, Ernesto; Palumbo, Manlio; Cignarella, Giorgio [Recueil des Travaux Chimiques des Pays-Bas, 1996, vol. 115, # 1, p. 25 - 30]

13
[ 2680-03-7 ]
[ 150-78-7 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
60%	With trifluoromethanesulfonic acid anhydride In 1,2-dichloro-ethane for 8h; Heating;
	With trifluoromethylsulfonic anhydride; potassium carbonate 1.) dichloroethane, reflux, 6 h, 2.) dichloroethane, ether, 1 h; Yield given. Multistep reaction;

Reference： [1]Nenajdenko, Valentine G.; Baraznenok, Ivan L.; Balenkova, Elizabeth S. [Tetrahedron Letters, 1996, vol. 37, # 24, p. 4199 - 4202]
[2]Nenajdenko, Valentine G.; Baraznenok, Ivan L.; Balenkova, Elizabeth S. [Tetrahedron, 1996, vol. 52, # 40, p. 12993 - 13006]

14
[ 52428-09-8 ]
[ 38998-05-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With perchloric acid; palladium 10% on activated carbon; hydrogen; acetic acid In water for 2.5h;
79%	With perchloric acid; hydrogen In acetic acid for 2.5h;
69.3%	With triethylsilane; trifluoroacetic acid at 10 - 20℃;	1.I Example-1; Compound No. 1; 3-[4-(7-Hydroxy-indan-4-yloxy)-3,5-dimethyl-pyrazol-1-yl]-propionic acid; STEP I: Preparation of 4,7-Dimethoxy indane; To the cooled and stirred suspension of 4,7-Dimethoxyindan-1-one (35 gm, 0.182 mole) in Triethyl silane (105.7 gm, 0.909 mole), added Trifluoroacetic acid (350 ml) at 10-15° C. The stirring was continued at room temperature for 2 hours and quenched into the water. It was extracted with Ethyl acetate. The Ethyl acetate layer was washed with Sodium bicarbonate solution, dried over Sodium sulphate and evaporated to give crude mass which was purified by column chouromatography using 5% Ethyl acetate in hexane (22.5 gm).Yield: 69.3%1H-NMR (400 MHz, CDCl3): δ 6.67 (2H, s), 3.70 (6H, s), 2.74-2.78 (4H, m), 1.95-2.02 (2H, m)

69.3%	With triethylsilane; trifluoroacetic acid at 10 - 20℃; for 2h;	1.I Example-1 : (Compound No. 1)3-[4-(7-Hydroxy-indan-4-yloxy)-3, 5-dimethyl-py razol-1 -yl]-propionic acidSTEP I: Preparation of 4, 7- Dimethoxy indane.; To the cooled and stirred suspension of 4,7-Dimethoxyindan-1-one (35gm,0.182 mole) in Triethyl silane (105.7 gm, 0.909mole ), added Trifluoroacetic acid (350 ml) at 10-15°C.The stirring was continued at room temperature for 2 hours and quenched into the water. It was extracted with Ethyl acetate. The Ethyl acetate layer was washed with Sodium bicarbonate solution, dried over Sodium sulphate and evaporated to give crude mass which was purified by column chouromatography using 5% Ethyl acetate in hexane (22.5 gm).Yield: 69.3%1H-NMR (400 MHz, CDCI3):δ 6.67(2H1 s),3.70(6H,s),2.74-2.78(4H,m),1.95- 2.02(2H, m)
55%	With triethylsilane; trifluoroacetic acid at 20℃; for 2h;

Reference： [1]Mejlsoe, Soren L.; Christensen, Jorn B. [Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057]
[2]Panetta, Charles A.; Sha, Dezhi; Torres, Epifanio; He, Zhuoli; Hussey; Fang, Zheng; Heimer, Norman E. [Synthesis, 1997, # 9, p. 1085 - 1090]
[3]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - US2010/168110, 2010, A1 Location in patent: Page/Page column 13
[4]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - WO2008/149379, 2008, A2 Location in patent: Page/Page column 36
[5]Kotha, Sambasivarao; Cheekatla, Subba Rao; Mandal, Binita [European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282]

15
[ 52428-09-8 ]
[ 16101-70-5 ]

Yield	Reaction Conditions	Operation in experiment
91.2%	With hydrogenchloride; isopentyl nitrite In methanol at 50 - 62℃; for 3h; Inert atmosphere;	31.1 Step 1) the preparation of compound 31-1 To a solution of compound 1-2 (2.48 g, 12.90 mmol) in anhydrous MeOH (10 mL) was added concentrated hydrochloric acid (2 mL) under N2. Then to the mixture was added isoamyl nitrite (6 mL) at 60-62 °C. The mixture was stirred at 50 °C for 3 hours, cooled to rt and filtered. The solid recrystallized from ethanol to afford the title compound 31-1 as a yellow solid (2.6 g, 91.2%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, DMSO-d6): δ 3.53 (s, 2H), 3.82 (d, 6H), 6.97 (d, J = 8.8 Hz, 1H), 7.29 (d, J = 8.8 Hz, 2H), 12.45 (s, 1H).
91.2%	With hydrogenchloride; Isovaleronitrile In methanol at 50 - 62℃; for 3h; Inert atmosphere;	31.1 the preparation of compound 31-1 To a solution of compound 1-2 (2.48 g, 12.90 mmol) in anhydrous MeOH (10 mL) was added concentratedhydrochloric acid (2 mL) under N2. Then to the mixture was added isoamyl nitrite (6 mL) at 60-62 °C. The mixture wasstirred at 50 °C for 3 hours, cooled to rt and filtered. The solid recrystallized from ethanol to afford the title compound31-1 as a yellow solid (2.6 g, 91.2%). The compound was characterized by the following spectroscopic data:1H NMR (400 MHz, DMSO-d6): δ 3.53 (s, 2H), 3.82 (d, 6H), 6.97 (d, J = 8.8 Hz, 1H), 7.29 (d, J = 8.8 Hz, 2H), 12.45(s, 1H).
	With hydrogenchloride; Isovaleronitrile 1.) MeOH, from 60 deg C to 62 deg C, 2.) MeOH, 50 deg C, 3 h; Yield given. Multistep reaction;

With hydrogenchloride; isopentyl nitrite In methanol; water at 40℃; for 1h;

Reference： [1]Current Patent Assignee: ZHANG (inventors); SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - EP2730572, 2015, B1 Location in patent: Paragraph 0544
[2]Current Patent Assignee: ZHANG (inventors); SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - EP2730572, 2015, B1 Location in patent: Paragraph 0543; 0544
[3]Panetta, Charles A.; Sha, Dezhi; Torres, Epifanio; He, Zhuoli; Hussey; Fang, Zheng; Heimer, Norman E. [Synthesis, 1997, # 9, p. 1085 - 1090]
[4]Location in patent: experimental part Colombo, Matteo; Vallese, Stefania; Peretto, Ilaria; Jacq, Xavier; Rain, Jean-Christophe; Colland, Frederic; Guedat, Philippe [ChemMedChem, 2010, vol. 5, # 4, p. 552 - 558]

16
[ 52428-09-8 ]
[ 253120-49-9 ]
[ 312273-15-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol for 0.5h; Heating;

Reference： [1]Chen, Junjie; Deady, Leslie W.; Desneves, Jose; Kaye, Anthony J.; Finlay, Graeme J.; Baguley, Bruce C.; Denny, William A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 10, p. 2461 - 2466]

17
[ 73568-29-3 ]
[ 52428-09-8 ]
2-[1-(2-Chloro-6-methoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,7-dimethoxy-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide In methanol at 20℃; for 12h;

Reference： [1]Charris, Jaime; Martinez, Patricia; Dominguez, Jose; Lopez, Simon; Angel, Jorge; Espinoza, Gustavo [Heterocyclic Communications, 2003, vol. 9, # 3, p. 251 - 256]

18
[ 68236-20-4 ]
[ 52428-09-8 ]
2-[1-(2-Chloro-7-methoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,7-dimethoxy-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium hydroxide In methanol at 20℃; for 12h;

Reference： [1]Charris, Jaime; Martinez, Patricia; Dominguez, Jose; Lopez, Simon; Angel, Jorge; Espinoza, Gustavo [Heterocyclic Communications, 2003, vol. 9, # 3, p. 251 - 256]

19
[ 68236-25-9 ]
[ 52428-09-8 ]
2-[1-(2-Chloro-5,6,7-trimethoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,7-dimethoxy-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium hydroxide In methanol at 20℃; for 12h;

Reference： [1]Charris, Jaime; Martinez, Patricia; Dominguez, Jose; Lopez, Simon; Angel, Jorge; Espinoza, Gustavo [Heterocyclic Communications, 2003, vol. 9, # 3, p. 251 - 256]

20
[ 52428-09-8 ]
(+/-)-2-iodo-4,7-dimethoxyindan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With iodine; Selectfluor In methanol at 22℃; for 5h;

Reference： [1]Jereb, Marjan; Stavber, Stojan; Zupan, Marko [Tetrahedron, 2003, vol. 59, # 31, p. 5935 - 5940]

21
[ 848610-51-5 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
32%	With scandium tris(trifluoromethanesulfonate) In nitromethane at 100℃; for 0.333333h;

Reference： [1]Fillion, Eric; Fishlock, Dan; Wilsily, Ashraf; Goll, Julie M. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1316 - 1327]

22
[ 68236-23-7 ]
[ 52428-09-8 ]
2-[1-(2-Chloro-6,7-dimethoxy-quinolin-3-yl)-meth-(E)-ylidene]-4,7-dimethoxy-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium methylate In methanol at 20℃;

Reference： [1]Charris, Jaime E.; Dominguez, Jos N.; Gamboa, Neira; Rodrigues, Juan R.; Angel, Jorge E. [European Journal of Medicinal Chemistry, 2005, vol. 40, # 9, p. 875 - 881]

23
[ 52428-09-8 ]
[ 615-43-0 ]
1,4-dimethoxy-5,10-dihydro-indeno[1,2-b]indole [ No CAS ]
[ 62-53-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 31 % Chromat. 2: 46 % Chromat.	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 40℃; for 3h; Irradiation;

Reference： [1]Barolo, Silvia M.; Rosales, Cecire; Angel Guio, Jorge E.; Rossi, Roberto A. [Journal of Heterocyclic Chemistry, 2006, vol. 43, # 3, p. 695 - 699]

24
[ 7677-24-9 ]
[ 52428-09-8 ]
[ 912342-39-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: trimethylsilyl cyanide; 4,7-dimethoxyindan-1-one With zinc(II) iodide In dichloromethane for 5h; Heating; Stage #2: With amberlyst-15 resin In benzene for 3h; Heating;

Reference： [1]McLean, Thomas H.; Parrish, Jason C.; Braden, Michael R.; Marona-Lewicka, Danuta; Gallardo-Godoy, Alejandra; Nichols, David E. [Journal of Medicinal Chemistry, 2006, vol. 49, # 19, p. 5794 - 5803]

25
[ 52428-09-8 ]
[ 40269-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaBH₄ / aq. ethanol / 0.5 h / Heating 2: 95 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 2.5 h / 20 °C
	Multi-step reaction with 2 steps 1: NaBH₄ / ethanol / 12 h / Ambient temperature 2: p-toluenesulfonic acid monohydrate / benzene / 0.5 h / Heating
	Multi-step reaction with 2 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h

Reference： [1]Zhang, Xiang; Thimmaiah, Muralidhara; Fang, Shiyue [Synthetic Communications, 2007, vol. 37, # 11, p. 1873 - 1877]
[2]Braun, Manfred; Bernhard, Carlo [Liebigs Annalen der Chemie, 1985, # 2, p. 435 - 437]
[3]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

26
[ 52428-09-8 ]
[ 1026431-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: ZnI₂ / CH₂Cl₂ / 5 h / Heating 1.2: 65 percent / Amberlyst-15 resin / benzene / 3 h / Heating 2.1: H₂ / Pd/C / ethanol / 0.33 h / 1034.3 Torr 2.2: H₂; NH₃ / Raney Ni / 6 h / 2327.17 Torr

27
[ 52428-09-8 ]
<i>C</i>-(5-bromo-4,7-dimethoxy-indan-1-yl)-methylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ZnI₂ / CH₂Cl₂ / 5 h / Heating 1.2: 65 percent / Amberlyst-15 resin / benzene / 3 h / Heating 2.1: H₂ / Pd/C / ethanol / 0.33 h / 1034.3 Torr 2.2: H₂; NH₃ / Raney Ni / 6 h / 2327.17 Torr 3.1: Br₂; acetic acid / 0.33 h

28
[ 93-02-7 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: piperidinium acetate / ethanol / 0.5 h 1.2: 57 percent / NaBH₃CN / ethanol / 0 - 20 °C 2.1: 32 percent / Sc(OTf)3 / nitromethane / 0.33 h / 100 °C
	Multi-step reaction with 3 steps 1: 79.5 percent / piperidine, piridine / 4 h / 110 °C 2: 100 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 24 h 3: 63 percent / polyphosphoric acid / 0.5 h / 57 - 60 °C
	Multi-step reaction with 2 steps 1: formic acid; triethylamine / 2 h / 0 - 100 °C 2: polyphosphoric acid / 4 h / 80 °C

	Multi-step reaction with 3 steps 1.1: pyridine; piperidine / 4.5 h / 50 °C / Reflux 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2068.65 Torr 3.1: thionyl chloride; N,N-dimethyl-formamide / 5 h / Reflux 3.2: 0.83 h / -5 °C
	Multi-step reaction with 2 steps 1: triethylamine / methanol / 5 h / 100 °C / Cooling with ice 2: polyphosphoric acid / 4 h / 80 °C
	Multi-step reaction with 3 steps 1: pyridine; piperidine; hydrogenchloride / water / Heating 2: palladium 10% on activated carbon; hydrogen / 760.05 Torr 3: phosphorus pentoxide; methanesulfonic acid / dichloromethane / 19 h / 20 °C

Reference： [1]Fillion, Eric; Fishlock, Dan; Wilsily, Ashraf; Goll, Julie M. [Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1316 - 1327]
[2]Gribkov, A.A.; Borovkov, V.V.; Evstigneeva, R.P.; Sakata, Y. [Chemistry of Heterocyclic Compounds, 1994, vol. 30, # 8, p. 905 - 915][Khimiya Geterotsiklicheskikh Soedinenii, 1993, # 8, p. 1052 - 1062]
[3]Current Patent Assignee: SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/82379, 2014, A1
[4]Mejlsoe, Soren L.; Christensen, Jorn B. [Journal of Heterocyclic Chemistry, 2014, vol. 51, # 4, p. 1051 - 1057]
[5]Current Patent Assignee: ZHANG (inventors); SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - EP2730572, 2015, B1
[6]Kotha, Sambasivarao; Cheekatla, Subba Rao; Mandal, Binita [European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282]

29
[ 52428-09-8 ]
[ 52457-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 79 percent / H₂, HClO₄ / 10percent Pd/C / acetic acid / 2.5 h / 2585.7 Torr 2: 84 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.42 h
	Multi-step reaction with 2 steps 1: trifluoroacetic acid; triethylsilane / 2 h / 20 °C 2: ammonium cerium (IV) nitrate / water; acetonitrile / 0.5 h / 0 °C

Reference： [1]Panetta, Charles A.; Sha, Dezhi; Torres, Epifanio; He, Zhuoli; Hussey; Fang, Zheng; Heimer, Norman E. [Synthesis, 1997, # 9, p. 1085 - 1090]
[2]Kotha, Sambasivarao; Cheekatla, Subba Rao; Mandal, Binita [European Journal of Organic Chemistry, 2017, vol. 2017, # 29, p. 4277 - 4282]

30
[ 52428-09-8 ]
2-(1-Benzyl-piperidin-4-ylmethyl)-4,7-dimethoxy-indan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) diisopropylamine, n-butyllithium, 2.) hexamethylphosphoric triamide 2: 76 percent / H₂ / 10percent Pd/C / tetrahydrofuran / 6 h / 760 Torr / Ambient temperature

Reference： [1]Sugimoto; Iimura; Yamanishi; Yamatsu [Journal of Medicinal Chemistry, 1995, vol. 38, # 24, p. 4821 - 4829]

31
[ 38489-74-6 ]
[ 52428-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / H₂ / 5percent Pd/C / tetrahydrofuran / 24 h 2: 63 percent / polyphosphoric acid / 0.5 h / 57 - 60 °C

32
[ 52428-09-8 ]
[ 136366-34-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 24.6 percent / NaH / tetrahydrofuran / 6 h / Heating 2: 97.3 percent / triethylsilane / trifluoroacetic acid / 0.5 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, -78 deg C, 1 h

Reference： [1]Tsue, Hirohito; Nakashima, Shuichi; Goto, Yasushi; Tatemitsu, Hitoshi; Misumi, Soichi; et al. [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 11, p. 3067 - 3075]

33
[ 52428-09-8 ]
[ 123676-80-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 39.2 percent / sodium hydride / tetrahydrofuran / 6 h / Heating 2: 35 percent / triethylsilane / trifluoroacetic acid / 0.5 h / Ambient temperature
	Multi-step reaction with 2 steps 1: 17 percent / NaH / tetrahydrofuran 2: 69 percent / CF₃COOH, Et₃SiH

Reference： [1]Tsue, Hirohito; Nakashima, Shuichi; Goto, Yasushi; Tatemitsu, Hitoshi; Misumi, Soichi; et al. [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 11, p. 3067 - 3075]
[2]Sakata; Nakashima; Goto; Tatemitsu; Misumi [Journal of the American Chemical Society, 1989, vol. 111, # 24, p. 8979 - 8981]

34
[ 52428-09-8 ]
[ 123676-81-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 39.2 percent / sodium hydride / tetrahydrofuran / 6 h / Heating 2: 35 percent / triethylsilane / trifluoroacetic acid / 0.5 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, -78 deg C, 1 h
	Multi-step reaction with 3 steps 1: 17 percent / NaH / tetrahydrofuran 2: 69 percent / CF₃COOH, Et₃SiH 3: 1.) BuLi / 1.) THF

35
[ 52428-09-8 ]
[ 160095-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 24.6 percent / NaH / tetrahydrofuran / 6 h / Heating 2: 97.3 percent / triethylsilane / trifluoroacetic acid / 0.5 h / Ambient temperature

Reference： [1]Tsue, Hirohito; Nakashima, Shuichi; Goto, Yasushi; Tatemitsu, Hitoshi; Misumi, Soichi; et al. [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 11, p. 3067 - 3075]

36
[ 52428-09-8 ]
5-(4,7-dimethoxy-2,2'-spirobiindan-5'-yl)-13,17-diethyl-2,3,7,8,12,18-hexamethyl-21H,23H-porphine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 39.2 percent / sodium hydride / tetrahydrofuran / 6 h / Heating 2: 35 percent / triethylsilane / trifluoroacetic acid / 0.5 h / Ambient temperature 3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, -78 deg C, 1 h 4: 42.1 percent / 47percent aq. HBr / methanol / 24 h / Heating

Reference： [1]Tsue, Hirohito; Nakashima, Shuichi; Goto, Yasushi; Tatemitsu, Hitoshi; Misumi, Soichi; et al. [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 11, p. 3067 - 3075]

37
[ 52428-09-8 ]
[ 79381-08-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating 6: 20percent aq. HCl / 2 h / Heating

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

38
[ 52428-09-8 ]
[ 81664-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature
	Multi-step reaction with 3 steps 1: 80 percent / NaH / tetrahydrofuran / 14 h 2: 74 percent / H₂, H⁽¹⁺⁾ 3: 95 percent / 2M NaOH, / methanol / 14 h / Ambient temperature

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]
[2]Khanna; Mitscher [Tetrahedron Letters, 1985, vol. 26, # 6, p. 691 - 694]

39
[ 52428-09-8 ]
2-Isocyanato-4,7-dimethoxy-indan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

40
[ 52428-09-8 ]
[ 81664-68-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

41
[ 52428-09-8 ]
4,7-Dimethoxy-indan-2-carbonyl azide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

42
[ 52428-09-8 ]
[ 81664-60-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating 6: 20percent aq. HCl / 2 h / Heating 7: 98 percent / 0.5 h

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

43
[ 52428-09-8 ]
N-methyl-2,3-dihydro-4,7-dimethoxy-1H-inden-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating 6: 20percent aq. HCl / 2 h / Heating 7: 98 percent / 0.5 h 8: KOH / acetone / 0.08 h / Heating

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

44
[ 52428-09-8 ]
N-isopropyl-2,3-dihydro-4,7-dimethoxy-1H-inden-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating 6: 20percent aq. HCl / 2 h / Heating 7: 64 percent / H₂ / PtO₂ / ethanol / 3 h / 2325.2 Torr / Ambient temperature

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

45
[ 52428-09-8 ]
RDS 127 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 78 percent / NaH / bis-(2-methoxy-ethyl) ether; benzene / 17 h / Ambient temperature 2: H₂, 70percent perchloric acid / 10percent Pd/C / acetic acid / 2 h / 2587.7 Torr 3: 48 percent / KOH, H₂O / ethanol / 5 h / Ambient temperature 4: 1.) Et₃N, ethyl chloroformate, 2.) sodium azide / 1.) acetone, H₂O, 0 deg C, 30 min, 2.) acetone, H₂O, 0 deg C, 90 min 5: toluene / 1 h / Heating 6: 20percent aq. HCl / 2 h / Heating 7: 1.) NaBH₄ / 1.) benzene, 5-10 deg C; 2.) benzene, reflux, 4 h

Reference： [1]Sindelar, R. D.; Mott, J.; Barfknecht, C. F.; Arneric, S. P.; Flynn, J. R.; et al. [Journal of Medicinal Chemistry, 1982, vol. 25, # 7, p. 858 - 864]

46
[ 52428-09-8 ]
[ 100848-78-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 72 percent / conc HCl / pyridine / 1.5 h / 165 - 170 °C 2: 2.) sodium sulfate, silver oxide / 1.) THf, ether, -75 deg C, 15 min, r.t., 45 min, 2.) r.t., 1 h 3: 77 percent / H₂ / 10percent Pd/C / ethanol / 0.25 h 4: 97 percent / sodium sulfate, silver oxide / benzene / 0.75 h / Ambient temperature

Reference： [1]Al-Hamdany, Raad; Bruce, J. Malcolm; Heatley, Frank; Khalafy, Jabbar [Journal of the Chemical Society. Perkin transactions II, 1985, p. 1395 - 1400]

47
[ 52428-09-8 ]
[ 100848-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 72 percent / conc HCl / pyridine / 1.5 h / 165 - 170 °C 2: 2.) sodium sulfate, silver oxide / 1.) THf, ether, -75 deg C, 15 min, r.t., 45 min, 2.) r.t., 1 h 3: 77 percent / H₂ / 10percent Pd/C / ethanol / 0.25 h

Reference： [1]Al-Hamdany, Raad; Bruce, J. Malcolm; Heatley, Frank; Khalafy, Jabbar [Journal of the Chemical Society. Perkin transactions II, 1985, p. 1395 - 1400]

48
[ 52428-09-8 ]
endo-4a,5,8,8a-tetrahydro-1-phenyl-5,8-methanobenz<f>indane-4,9-quinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 72 percent / conc HCl / pyridine / 1.5 h / 165 - 170 °C 2: 2.) sodium sulfate, silver oxide / 1.) THf, ether, -75 deg C, 15 min, r.t., 45 min, 2.) r.t., 1 h 3: 77 percent / H₂ / 10percent Pd/C / ethanol / 0.25 h 4: 97 percent / sodium sulfate, silver oxide / benzene / 0.75 h / Ambient temperature 5: 100 percent / 1.5 h / Ambient temperature

Reference： [1]Al-Hamdany, Raad; Bruce, J. Malcolm; Heatley, Frank; Khalafy, Jabbar [Journal of the Chemical Society. Perkin transactions II, 1985, p. 1395 - 1400]

49
[ 52428-09-8 ]
[ 123676-88-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 17 percent / NaH / tetrahydrofuran 2: 69 percent / CF₃COOH, Et₃SiH 3: 1.) BuLi / 1.) THF 4: 42 percent / HBr / methanol

Reference： [1]Sakata; Nakashima; Goto; Tatemitsu; Misumi [Journal of the American Chemical Society, 1989, vol. 111, # 24, p. 8979 - 8981]

50
[ 52428-09-8 ]
(1R,1aR,6aS)-2,5-Dimethoxy-1,1a,6,6a-tetrahydro-cyclopropa[a]indene-1-carbonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C 4: 640 mg / ethanol. NaOH 5: SOCl₂ / CH₂Cl₂

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

51
[ 52428-09-8 ]
exo-1,1a,6,6a-tetrahydro-2,5-dimethoxycycloprop<a>indene-1-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C 4: 640 mg / ethanol. NaOH

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

52
[ 52428-09-8 ]
(1S,1aS,6aR)-2,5-Dimethoxy-1,1a,6,6a-tetrahydro-cyclopropa[a]indene-1-carbonyl azide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C 4: 640 mg / ethanol. NaOH 5: SOCl₂ / CH₂Cl₂ 6: 510 mg / sodium azide / acetone; H₂O / 25 °C

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

53
[ 52428-09-8 ]
((1S,1aS,6aS)-2,5-Dimethoxy-1,1a,6,6a-tetrahydro-cyclopropa[a]inden-1-yl)-carbamic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C 4: 640 mg / ethanol. NaOH 5: SOCl₂ / CH₂Cl₂ 6: 510 mg / sodium azide / acetone; H₂O / 25 °C 7: 505 mg / toluene / Heating

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

54
[ 52428-09-8 ]
[ 79381-04-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C 4: 640 mg / ethanol. NaOH 5: SOCl₂ / CH₂Cl₂ 6: 510 mg / sodium azide / acetone; H₂O / 25 °C 7: 505 mg / toluene / Heating 8: 72 percent / H₂, conc. HCl / 10percent Pd/C / ethanol / 0.75 h / 2585.7 Torr

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

55
[ 52428-09-8 ]
[ 79381-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 63 percent / CuSO₄ / toluene; xylene / 75 °C

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

56
[ 52428-09-8 ]
[ 79381-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 100 percent / NaBH₄ / methanol / 0.5 h / 25 °C 2: 48 percent / SOCl₂, pyridine / 1.) 25 deg C, 30 min, 2.) reflux, 2 h 3: 15 percent / CuSO₄ / toluene; xylene / 75 °C

Reference： [1]DeMarinis, R. M.; Bryan, W. M.; Shah, D. H.; Hieble, J. P.; Pendleton, R. G. [Journal of Medicinal Chemistry, 1981, vol. 24, # 12, p. 1432 - 1437]

57
[ 52428-09-8 ]
[ 96642-71-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 80 percent / NaH / tetrahydrofuran / 14 h 2: 74 percent / H₂, H⁽¹⁺⁾ 3: 95 percent / 2M NaOH, / methanol / 14 h / Ambient temperature 4: diethyl ether / 3 h / Ambient temperature 5: 49 percent / NaCl / ALCl₃ / 0.12 h / 180 °C