Name: 139122-19-3|4-(2-Hydroxyethyl)indolin-2-one|98%
Brand: Ambeed
SKU: A210973
Price: 10.0 USD
Availability: InStock
Rating: 99 (32 reviews)

1
[ 124-63-0 ]
[ 139122-19-3 ]
[ 139122-21-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With pyridine; In dichloromethane; at 20℃;	Reference Example 36 Preparation of 2-(2-oxoindolin-4-yl)ethyl methanesulfonate <strong>[139122-19-3]4-(2-hydroxyethyl)indolin-2-one</strong> 36-a (500 mg, 2.822 mmol) was dissolved in dichloromethane (15 ml) and pyridine (335 mg, 4.233 mmol) was added. Methanesulfonyl chloride (356 mg, 3.104 mmol) was added dropwise thereto at 0 C. followed by stirring at room temperature overnight. The mixture was diluted with dichloromethane (15 ml), washed with 1N hydrochloric acid, water, and brine sequentially. The organic phase was dried over anhydrous sodium sulfate, concentrated and subjected to column chromatography to obtain a yellow solid (460 mg, yield: 64%). ESI-MS (m/z): 256.0 [M+H]+.

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Patent: US2017/158680,2017,A1 .Location in patent: Paragraph 0487; 0488

2
[ 98-09-9 ]
[ 139122-19-3 ]
[ 139122-22-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

3
[ 98-59-9 ]
[ 139122-19-3 ]
[ 139122-20-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With pyridine; In dichloromethane; at 5 - 10℃; for 3h;	To the reaction flask was added 50mL Compound 14 (2.00g, 11.29mmol), 13mLPy, stirred, dropwise below 5 deg C to 15mL methylene chloride added 3.02g (15.84mmol) TsCl. Bi drops under 10 degt C and stirred for 3h, the reaction was complete. Dropping20mL water, 9mL dichloromethane, 15mL of concentrated hydrochloric acid, followed by stirring for 2h standing separated and the aqueous phase extracted with dichloromethane (40mL × 2), togetherThe organic layer was washed with water, dried over anhydrous sodium sulfate overnight. The filtrate was distilled to just appear solid particles, cooling crystallization, filtration, drying,Pale yellow solid 3.22g. Yield 86%, mp: 128-129
86%	In pyridine; dichloromethane; at 5 - 10℃; for 3h;	To the reaction flask was added compound 8 (2.00g, 11.29mmol), 13mLPy, stirring, 5 lower than 15mL dichloromethane dropwise diluted 3.02g (15.84mmol) TsCl. Bi drops under 10 stirred for 3h, the reaction was complete. 20mL water was added dropwise, 9mL dichloromethane, 15mL of concentrated hydrochloric acid, stirred 2h standing separated and the aqueous phase extracted with dichloromethane (40mL × 2), the organic layers combined, washed with water, dried over anhydrous sodium sulfate overnight. The filtrate was distilled to just appear solid particles, cooling crystallization, filtration, and dried to give a pale yellow solid 3.22g. Yield 86%, mp: 128-129 .
	With pyridine; at 20℃; for 2h;	using a dry round bottom flask as a reaction vessel,One equivalent of Compound 5 is dissolved in one or more of dichloromethane/chloroform/1,2-dichloroethane/pyridine (subject to complete dissolution),1.2 equivalents of pyridine were added at room temperature, and 1.2 equivalents of p-toluenesulfonyl chloride were added thereto, and the reaction was further stirred for about 2 hours.The reaction was completely monitored by TLC. The reaction was quenched with 1N hydrochloric acid and extracted three times with ethyl acetate.The combined organic phase was extracted with saturated brine and dried over anhydrous sodium sulfate.Compound 6 was obtained.

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Organic Process Research and Development,1998,vol. 2,p. 3 - 9
[3]Patent: CN105461608,2016,A .Location in patent: Paragraph 0068; 0069
[4]Patent: CN105418482,2016,A .Location in patent: Paragraph 0051; 0052
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609
[6]MedChemComm,2014,vol. 5,p. 891 - 898
[7]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738
[8]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[9]Patent: CN108440376,2018,A .Location in patent: Paragraph 0062; 0063; 0064

4
[ 168476-61-7 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

5
[ 139122-18-2 ]
[ 139122-19-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With water; sodium hydroxide; In methanol; for 4h;Reflux;	To the reaction flask were successively added 8.10g (28.79mmol) methanol compound 7,40mL, 40mLH2O, mix, then add 1.5gNaOH, after completion of the reaction was refluxed for 4h. Methanol was distilled off under reduced pressure, to remove the remaining mixture was cooled to room temperature, 1% sulfuric acid with pH value adjusted to 7 to give a pasty white solid was filtered, washed with cold water (40mL × 2), and dried in vacuo at 80 deg.] C to give 4.85 g of the white solid, yield 95%, m.p. 146-148 .

Reference： [1]Patent: CN105418482,2016,A .Location in patent: Paragraph 0048; 0049; 0050
[2]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[3]Organic Process Research and Development,1998,vol. 2,p. 3 - 9
[4]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144

6
[ 139122-19-3 ]
[ 358732-52-2 ]
1-[4-(2-hydroxy-ethyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.5 g (28%)		1-[4-(2-Hydroxy-ethyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 4-(2-Hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.1 g, 0.6 mmol) was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde (1.2 eq, 0.06 g) to give 0.5 g (28%) of the title compound as a yellow solid. 1H NMR (300 MHz, DMSO-d6) delta 13.87 (s, 1H, N), 11.07 (s, 1H, N-CO), 7.90 (d, J=3.0Hz, 1H), 7.55 (s, 1H, C=C), 7.09 (m, 1H), 6.84 (d, J=7.6Hz, 1H), 6.76 (d, J=7.7Hz, 1H), 4.89 (t, J=4.8Hz, 1H, CH2CH2O), 4.49 (t, J=6.0Hz, 2H, CO2C2CH2pyrrole), 3.70 (m, 2H, HOCH2C2Ar and CO2CH2C2pyrrole).MS m/z 325.2 [M++1].

Reference： [1]Patent: US2002/42427,2002,A1
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1939 - 1942

7
[ 139122-19-3 ]
[ 358732-55-5 ]
1-[4-(2-hydroxy-ethyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1939 - 1942

8
[ 493-05-0 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[3]Patent: CN105461608,2016,A
[4]Patent: CN105418482,2016,A
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609

9
[ 22901-09-3 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

10
[ 95033-78-6 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

11
[ 139122-19-3 ]
[ 91374-21-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[3]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[4]Patent: CN108440376,2018,A

12
[ 139122-19-3 ]
4-ethylenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[3]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

13
[ 120427-96-5 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

14
2-(2-hydroxyethyl)-β-nitrostyrene [ No CAS ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

15
2-(2-bromoethyl)-β-nitrostyrene [ No CAS ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

16
[ 120427-95-4 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

17
[ 168476-58-2 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[3]Patent: CN105461608,2016,A
[4]Patent: CN105418482,2016,A
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609

18
[ 139122-15-9 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[2]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[3]Patent: CN105461608,2016,A
[4]Patent: CN105418482,2016,A
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609

19
[ 168476-57-1 ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

20
2-(2-benzoyloxyethyl)-β-nitrostyrene [ No CAS ]
[ 139122-19-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882

21
[ 139122-17-1 ]
[ 139122-19-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		3-Chloro-4-[2-(phenylcarbonyloxy)ethyl]-2-oxindole (1.2 g, 4 mmol), 0.15 g of 5% palladium on carbon and 15 mL of methanol was stirred and heated to reflux and 0.4 g (8 mmol) of hydrazine hydrate was slowly added at a rate to control refluxing. The reaction was refluxed for 1 hour, 0.33 g of sodium hydroxide dissolved in 6.6 mL of water was added, and the mixture refluxed for an additional 30 minutes. The hot solution was filtered through a pad of diatomaceous earth to remove the catalyst and distilled to remove most of the methanol solvent. The aqueous residue was allowed to stand overnight at room temperature and then in the refrigerator for 2 hours. The white solids were collected by vacuum filtration, washed twice with water, and dried under vacuum to give 6 g (84% yield) of the title compound, mp 145.1-147.0 C.
71%		To 15 ml methanol by adding intermediate 13 (1.20g, 3 . 80mmol), stirred, and added 10% Pd/C (0.075g, 0 . 070mmol), heated to reflux. Slowly dripped in the hydrazine hydrate (0.38g, 7 . 59mmol), refluxed for 3h. Dissolved in 26 ml of water sodium hydroxide (8.10g, 202mmol), and then refluxed for 2h. Hot filtered, concentrated under reduced pressure to remove most of the methanol (solution just beginning to separate out with solid particles), is arranged in the refrigerator in which the cooling 2h. Filtering, cold water wash (2×15 ml), 65 C vacuum drying, to obtain colourless crystal 0.48 g. Yield 71%, melting point 146-147 C (literature 147-149 C).

Reference： [1]Patent: US2004/186160,2004,A1 .Location in patent: Page/Page column 22-23
[2]Patent: CN105461608,2016,A .Location in patent: Paragraph 0065; 0066; 0067
[3]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609
[4]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 875 - 882
[5]Organic Process Research and Development,1998,vol. 2,p. 3 - 9
[6]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[7]Patent: CN105418482,2016,A

22
[ 760998-29-6 ]
[ 139122-19-3 ]
3-{2-[4-(2-hydroxyethyl)-2-oxo-1,2-dihydroindol-(3Z)-ylidenemethyl]-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-3-yl}propionic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ethanol;	2-Hydroxyethyl-oxindole was condensed with 3-(2-formyl-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrol-3-yl)-propionic acid and piperidine in ethanol to give the title compound. MS (m/z) 395 [M+1].

Reference： [1]Patent: US2004/186160,2004,A1 .Location in patent: Page/Page column 35

23
[ 760998-31-0 ]
[ 139122-19-3 ]
4-(2-hydroxyethyl)-3-[1-[3-(3-hydroxypropyl)-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrol-2-yl]meth-(Z)-ylidene]-1,3-dihydroindol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ethanol;	4-(2-Hydroxyethyl)-oxindole was condensed with 3-(3-hydroxy-propyl)-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-2-carbaldehyde and piperidine in ethanol to give the title compound. MS (m/z) 381 [M+1].

Reference： [1]Patent: US2004/186160,2004,A1 .Location in patent: Page/Page column 39

24
[ 150-76-5 ]
[ 139122-19-3 ]
4-[2-(4-methoxy-phenoxy)-ethyl]-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 18h;	Diethyl azodicarboxylate (0.47 mL, 3 mmol) was added to a solution of triphenylphosphine (0.786 g, 3 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) followed by 4-methoxyphenol (0.372 g, 3 mmol). The mixture was stirred at room temperature for 18 hours and the solvent was evaporated. The residue was dissolved in ethyl acetate (150 mL) and the organic solvent was washed with 2 N hydrochloric acid (3*30 mL), saturated sodium bicarbonate solution and brine. The residue was chromatographed on silica gel eluding with ethyl acetate:hexane 2:8 to give 0.14 g (16%) 4-[2-(4-Methoxy-phenoxy)-ethyl]-1,3-dihydro-indol-2-one. 1H-NMR (300 MHz, DMSO-d6) delta 10.33 (s, br, 1H, NH), 7.10 (t, J=7.8 Hz, 1H, Ar-H), 6.83-6,87 (m, 5H, Ar-H), 6.67 (d, J=7.5 Hz, 1H, Ar-H), 4.10 (t, J=6.9 Hz, 2H, OCH2CH2), 3.67 (s, 3H, OCH3), 3.49 (s, 2H, CH2, H-3), 2.91 (t, J=6.9 Hz, 2H, OCH2CH2).

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 92

25
[ 139122-19-3 ]
[ 74-88-4 ]
4-(2-methoxy-ethyl)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20℃; for 2h;	Methyl iodide (1.41 g, 10 mmol) was added to a stirred mixture of silver trifluoromethanesulfonate (2.56 g, 10 mmol) and 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.88 g, 5 mmol) in dichloromethane (20 mL) at 0 C. The precipitate formed after 5-10 minutes changed color from yellow to gray then dark purple. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with dichloromethane and filtered through celite. The filtrate was concentrated and chromatographed on silica gel to give 4-(2-methoxy-ethyl)-1,3-dihydro-indol-2-one. 1H-NMR (360 MHz, DMSO-d6) delta 10.27 (s, br, 1H, NH), 7.07 (t, J=7.6 Hz, 1H, Ar-H), 6.78 (d, J=7.6 Hz, 1H, Ar-H), 6.65 (d, J=7.6 Hz, 1H, Ar-H), 3.51 (t, J=6.7 Hz, 2H, OCH2CH2), 3.42 (s, 2H, H-3, CH2), 3.22 (s, 3H, OCH3), 2.71 (t, J=6.7 Hz, 2H, OCH2CH2). MS-EI 191 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 92

26
[ 1121-60-4 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-pyridin-2-ylmethylene-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With piperidine; In ethanol; at 90℃; for 8h;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (80 mg, 0.45 mmol) and 2-pyridinecarboxaldehyde (60 mg, 0.56 mmol) in 1% of piperidine in ethanol (5 mL) was heated at 90 C. for 8 hours. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel. It was then triturated with ethyl acetate and hexane to give 55 mg (46%) of 4-(2-hydroxy-ethyl)-3-pyridin-2-ylmethylene-1,3-dihydro-indol-2-one. 1H-NMR (360 MHz, DMSO-d6) delta 10.58 (s, br, 1H, NH), 8.64 (d, J=4.7 Hz, 1H, Ar-H), 8.40 (d, J=8.3 Hz, 1H), 7.81 (dt, J=1.8 & 7.7 Hz, 1H, Ar-H), 7.7 (s, 1H, H-vinyl), 7.34 (m, 1H, Ar-H), 7.16 (t, J=7.6 Hz, 1H), 6.83 (d, J=7.6 Hz, 1H, Ar-H), 6.69 (d, J=7.6 Hz, 1H, Ar-H), 4.80 (t, J=5.2 Hz, 1H, OH), 3.71 (m, 2H, -CH2CH2OH), 3.03 (t, J=7.2 Hz, 2H, -CH2CH2OH). MS-EI 267 [M+1]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 83

27
[ 103-71-9 ]
[ 139122-19-3 ]
[ 295799-05-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 70℃; for 15h;	Phenyl isocyanate (0.652 mL, 6 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops). The mixture was heated at 70 C. for 15 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 953 mg (80%) of phenyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as an off-white powder. 1H-NMR (360 MHz, DMSO-d6) delta 10.30 (s, br, 1H, NH), 9.52 (s, br, 1H, NH), 7.42 (d, J=7.9 Hz, 2H, Ar-H), 7.24 (m, 2H, Ar-H), 7.11 (t, J=7.5 Hz, 1H, Ar-H), 6.96 (m, 1H, Ar-H), 6.84 (d, J=7.5 Hz, 1H, Ar-H), 6.69 (d, J=7.5 Hz, 1H, Ar-H), 4.28 (t, J=6.8 Hz, 2H, OCH2CH2), 3.48 (s, 2H, H-3), 2.85 (t, J=6.8 Hz, 2H, OCH2CH2). MS-EI 296 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 88

28
[ 103-72-0 ]
[ 139122-19-3 ]
[ 295799-03-0 ]

Yield	Reaction Conditions	Operation in experiment
58%		Phenyl isothiocyanate (0.45 mL, 3.75 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (443 mg, 2.5 mmol) in tetrahydrofuran (5 mL). The mixture was stirred at room temperature for 20 hours and then 70 C. for 8 hours. One mL of dimethylforamide was added to the mixture to make it homogenous and the heating was continued for another 42 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 452 mg (58%) of phenyl-thiocarbamic acid O-[2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl]ester as a white solid. 1H-NMR (360 MHz, DMSO-d6) delta 11.00 (s, br, 1H, NH), 10.30 (s, br, 1H, NH), 7.58 (s, br, 1H, Ar-H), 7.25 (s, br, 3H, Ar-H), 7.11 (t, J=7.9 Hz, 2H, Ar-H), 6.85 (m, 1H, Ar-H), 6.68 (d, J=7.2 Hz, 1H, Ar-H), 4.67 (m, 2H, OCH2CH2), 3.27 (s, 2H, H-3), 2.95 (m, 2H, OCH2CH2). MS-EI 312 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 87

29
[ 139122-19-3 ]
[ 109-90-0 ]
ethyl-carbamic acid-2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 80℃; for 48h;	Ethyl isocyanate (0.633 mL, 8 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL) and dimethylforamide (2 mL) under nitrogen atmosphere. The mixture was heated at 80 C. for 48 hours. The reaction was cooled, poured into water (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel eluding with ethyl acetate/hexane to give 158 mg (16%) of ethyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as a white powder. 1H-NMR (360 MHz, DMSO-d6) delta 10.28 (s, br, 1H, NH), 7.08 (t, J=7.7 Hz, 1H, Ar-H), 7.03 (m, br, 1H, NH), 6.78 (d, J=7.7 Hz, 1H, Ar-H), 6.64 (d, J=7.7 Hz, 1H, Ar-H), 4.10 (t, J=6.5 Hz, 2H, OCH2CH2), 3.43 (s, 2H, H-3), 2.91-2.99 (m, 2H, CH2CH3), 2.74 (t, J=6.5 Hz, 2H, OCH2CH2), 0.96 (t, J=7.3 Hz, 3H, CH2CH3). MS-EI 248 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 91

30
[ 139122-19-3 ]
[ 2845-62-7 ]
[ 295799-11-0 ]

Yield	Reaction Conditions	Operation in experiment
27%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 80℃; for 15h;	Benzene sulfonyl isocyanate (1.07 mL, 8 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops) under nitrogen atmosphere. The mixture was heated at 80 C. for 15 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was discarded and the basic aqueous layer was acidified with 6 N hydrochloric acid (18 mL) followed by extraction into ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 390 mg (27%) of benzene sulfonyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as an off-white powder. 1H-NMR (360 MHz, DMSO-d6) delta 12.03 (s, br, 1H, NH), 10.30 (s, br, 1H, NH), 7.83 (d, J=7.2 Hz, 2H, Ar-H), 7.68-7.72 (m, 1H, Ar-H), 7.58-7.62 (m, 2H, Ar-H), 7.05 (t, J=7.7 Hz, 1H), 6.71 (d, J=7.7 Hz, 1H), 6.64 (d, J=7.7 Hz, 1H), 4.17 (t, J=6.3 Hz, 2H, OCH2CH2), 3.42 (s, 2H, H-3), 2.71 (t, J=6.3 Hz, 2H, OCH2CH2). MS 360 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 90

31
[ 580-51-8 ]
[ 139122-19-3 ]
[ 295798-89-9 ]

Yield	Reaction Conditions	Operation in experiment
36%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24h;	Diethyl azodicarboxylate (1.58 mL, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 3-phenylphenol (1.7 g, 10 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was dissolved in ethyl acetate (150 mL) and the organic solvent was washed with 2 N hydrochloric acid (3*50 mL), saturated sodium bicarbonate solution and brine. The residue was chromatographed on silica gel eluding with ethyl acetate: hexane 2:8 to give 1.19 g (36%) of 4-[2-(biphenyl-3-yloxy)-ethyl]-1,3-dihydro-indol-2-one. 1H-NMR (360 MHz, DMSO-d6) delta 10.30 (s, br, 1H, NH), 7.63-7.65 (m, 2H, Ar-H), 7.41-7.45 (m, 2H, Ar-H), 7.32-7.36 (m, 2H, Ar-H), 7.2 (m, 1H, Ar-H), 7.16 (m, 1H, Ar-H), 7.12 (t, J=7.9 Hz, 1H, Ar-H), 6.89-6.93 (m, 2H, Ar-H), 6.68 (d, J=7.2 Hz, 1H, Ar-H), 4.26 (t, J=6.8 Hz, 2H, CH2CH2O), 3.52 (s, 2H, H-3, CH2), 2.98 (t, J=6.8 Hz, 2H, CH2CH2O).

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 82

32
[ 1122-91-4 ]
[ 139122-19-3 ]
3-(4-bromobenzylidene)-4-(2-hydroxy-ethyl)-1,3-dihydroindol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With piperidine; In ethanol; at 90℃;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (3.0 g, 17 mmol), 4-bromobenzaldehyde (3.1 g, 17 mmol) and piperidine (8.4 mL, 85 mmol) in ethanol (113 mL) was heated at 90 C. for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 2.4 g (41%) of 3-(4-bromo-benzylidene)-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one as a yellow orange solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.53 (s, 1H, NH), 7.96 (d, J=7.4 Hz, 2H), 7.69 (s, 1H, H-vinyl), 7.61 (d, J=7.4 Hz, 2H, Ar-H), 7.12 (m, 1H, Ar-H), 6.81 (d, J=7.4 Hz, 1H, Ar-H), 6.67 (d, J=7.4 Hz, 1H, Ar-H), 4.80 (m, 1H, OH), 3.69 (m, 2H, CH2CH2OH), 3.04 (m, 2H, CH2CH2OH). MS-EI 343/345 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 82-83

33
[ 3173-53-3 ]
[ 139122-19-3 ]
cyclohexyl-carbamic acid-2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 70 - 85℃; for 64h;	Cyclohexyl isocyanate (0.766 mL, 6 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops). The mixture was heated at 70 C. for 16 hours. 0.511 mL of cyclohexyl isocyanate was added to the reaction and continued to heat at 80 C. for 24 hours. More cyclohexyl isocyanate (0.255 mL) was added and continued to heat at 85 C. for 24 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 317 mg of the product. A second crop of product (32 mg) was obtained from the mother liquor followed by column chromatography (1:1 ethyl acetate:hexane). A total of 349 mg (29%) of cyclohexyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as a white powder was obtained. 1H-NMR (360 MHz, DMSO-d6) delta 10.28 (s, br, 1H, NH), 7.09 (t, J=7.6 Hz, 1H, Ar-H), 6.97 (d, br, J=6.6 Hz, 1H, CONHCH), 6.79 (d, J=7.6 Hz, 1H, Ar-H), 6.65 (d, J=7.6 Hz, 1H, Ar-H), 4.11 (t, J=6.6 Hz, 2H, OCH2CH2), 3.44 (s, 2H, H-3), 3.25-3.35 (m, 1H, CONHCH), 2.75 (t, J=6.6 Hz, 2H, OCH2CH2), 1.5-1.8 (m, c-hexyl). MS-EI 302 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 89

34
[ 17337-13-2 ]
[ 139122-19-3 ]
biphenyl-2-yl-carbamic acid-2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 80℃; for 15h;	2-Biphenylyl isocyanate (1.15 mL, 6.7 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops) under nitrogen atmosphere. The mixture was heated at 80 C. for 15 hours. The reaction was cooled, quenched with 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel eluding with ethyl acetate:hexane 3:2 to give 1.188 g (80%) of biphenyl-2-yl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as a white fluffy solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.28 (s, br, 1H, NH), 8.57 (s, 1H, NH), 7.25-7.41 (m, 9H, Ar-H), 7.08 (t, J=7.6 Hz, 1H, Ar-H), 6.73 (d, J=7.6 Hz, 1H, Ar-H), 6.66 (d, J=7.6 Hz, 1H, Ar-H), 4.09 (t, J=6.4 Hz, 2H, OCH2CH2), 3.35 (s, 2H, CH2, H-3), 2.69 (t, J=6.4 Hz, 2H, OCH2CH2). MS-EI 372 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 90-91

35
[ 139122-19-3 ]
[ 1609-86-5 ]
[ 295799-07-4 ]

Yield	Reaction Conditions	Operation in experiment
12%	With pyridine; In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 70 - 90℃; for 115h;	Tert-butyl isocyanate (0.685 mL, 6 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops). The mixture was heated at 70 C. for 15 hours and 80 C. for 39 hours. 0.457 mL of tert-butyl isocyanate was added to the reaction and continued to heat at 90 C. for 24 hours. More tert-butyl isocyanate (0.457 mL) was added and continued to heat at 90 C. for 37 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 130 mg (12%) of tert-butyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester. 1H-NMR (300 MHz, DMSO-d6) delta 10.30 (s, br, 1H, NH), 7.09 (t, J=7.6 Hz, 1H, Ar-H), 6.81 (s, 1H, NHC(CH3)3, 6.80 (d, J=7.6 Hz, 1H, Ar-H), 6.65 (d, J=7.6 Hz, 1H, Ar-H), 4.07 (m, 2H, OCH2CH2), 3.45 (s, 2H, H-3), 2.73-2.74 (m, 2H, OCH2CH2), 1.18 (s, 3H, 3*CH3). MS-EI 276 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 88-89

36
[ 139122-19-3 ]
[ 1795-48-8 ]
isopropyl-carbamic acid-2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	In tetrahydrofuran; DMF (N,N-dimethyl-formamide); at 80℃; for 64h;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (3 g, 16.93 mmol) and isopropyl isocyanate (2.49 mL, 25.40 mmol) in tetrahydrofuran (16 mL) and dimethylformamide (6 mL) was heated at 80 C. for 64 hours. The reaction mixture was poured into water and extracted with ethyl acetate (400 mL), washed with brine, dried (sodium sulfate), and concentrated. The residue was recrystallized form methanol, ethyl acetate and hexanes to give 1.136 g (26%) of isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as crystalline solid.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 97

37
[ 75-03-6 ]
[ 139122-19-3 ]
4-(2-ethoxy-ethyl)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20℃; for 2h;	Ethyl iodide (o.47 mL, 6 mmol) was added to a stirred mixture of silver trifluoromethanesulfonate (1.35 g, 5.2 mmol) 2,6-di-tert-butylpyridine (1 g, 5.2 mmol) and 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) in dichloromethane (10 mL) at 0 C. The mixture was warmed to room temperature and stirred for 2 hours. The precipitate formed after 5-10 minutes changed color from yellow to brown. The reaction mixture was diluted with dichloromethane (100 mL) and washed with 1 N hydrochloric acid, saturated sodium bicarbonate and brine, dried and concentrated. The residue was chromatographed on silica gel to give 180 mg (29%) of 4-(2-ethoxy-ethyl)-1,3-dihydro-indol-2-one as a purple oil. 1H-NMR (360 MHz, DMSO-d6) delta 10.27 (s, br, 1H, NH), 7.07 (t, J=7.8 Hz, 1H, Ar-H), 6.78 (d, J=7.8 Hz, 1H, Ar-H), 6.65 (d, J=7.8 Hz, 1H, Ar-H), 3.54 (t, J=6.9 Hz, 2H, OCH2CH2), 3.38-3.45 (m, 2H, OCH2CH3), 3.43 (s, 2H, H-3, CH2), 2.71 (t, J=6.9 Hz, 2H, OCH2CH2), 1.07 (t, J=7.0 Hz, 3H, OCH2CH3). MS 206.2 [M+]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 93

38
[ 88-69-7 ]
[ 139122-19-3 ]
[ 295798-87-7 ]

Yield	Reaction Conditions	Operation in experiment
9%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 18h;	Diethyl azodicarboxylate (1.58 mL, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 2-isopropylphenol (1.36 mL, 10 mmol). The mixture was stirred at room temperature for 18 hours and the solvent was evaporated. The residue was chromatographed on silica gel eluding with ethyl acetate: hexane 2:8 to give 0.26 g (9%) of 4-[2-(2-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one as a light yellow solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.29 (s, br, 1H, NH), 7.08-7.14 (m, 3H, Ar-H), 6.83-6.93 (m, 3H, Ar-H), 6.67 (d, J=7.2 Hz, 1H, Ar-H), 4.18 (t, J=6.4 Hz, 2H, CH2CH2O), 3.47 (s, 2H, H-3, CH2), 3.11 (m, 1H, CH(CH3)2), 2.96 (t, J=6.4 Hz, 2H, CH2CH2O), 1.05 (d, J=6.8 Hz, 6H, CH(CH3)2). MS-EI 295 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 81-82

39
[ 99-89-8 ]
[ 139122-19-3 ]
[ 295799-23-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24h;	Diethyl azodicarboxylate (1.58 mL, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 4-isopropylphenol (1.36 g, 10 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was chromatographed on silica gel eluding with ethyl acetate:hexane 2:8 to give 1.1 g (37%) of 4-[2-(4-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one as a light yellow solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.30 (s, br, 1H, NH), 7.11 (d, J=7.2 Hz, 2H), 7.1 (t, J=7.6 Hz, 1H, Ar-H), 6.87 (d, J=7.6 Hz, 1H), 6.82 (d, J=7.2 Hz, 2H, Ar-H), 6.68 (d, J=7.6 Hz, 1H, Ar-H), 4.14 (t, J=6.8 Hz, 2H, CH2CH2O), 3.49 (s, 2H, H-3, CH2), 2.93 (t, J=6.8 Hz, 2H, CH2CH2O), 2.81 (m, 1H, CH(CH3)2), 1.15 (d, J=6.5 Hz, 6H, CH(CH3)2). MS-EI 295 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 93-94

40
[ 618-45-1 ]
[ 139122-19-3 ]
[ 295798-85-5 ]

Yield	Reaction Conditions	Operation in experiment
14%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 24h;	Diethyl azodicarboxylate (0.47 mL, 3 mmol) was added to a solution of triphenylphosphine (0.786 g, 3 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (0.53 g, 3 mmol) (Hayler, J. D.; Howic, S. L. B.; Giles, R. G.; Negus, A.; Oxley, P. W.; et al; J. Heteocycl. Chem.; 32; 3; 1995; 875-882), followed by 3-isopropylphenol (0.41 mL, 3 mmol). The mixture was stirred at room temperature for one day and the solvent was evaporated. The residue was chromatographed on silica gel eluding with ethyl acetate: hexane 1:9 to give 120 mg (14%) of 4-[2-(3-isopropyl-phenoxy)-ethyl]-1,3-dihydro-indol-2-one. 1H-NMR (360 MHz, DMSO-d6) delta 10.31 (s, br, 1H, NH), 7.09-7.12 (m, 2H, Ar-H), 6.88 (d, J=7.6 Hz, 1H, Ar-H), 6.67-6.79 (m, 4H, Ar-H), 4.16 (t, J=6.7 Hz, 2H, OCH2CH2), 3.5 (s, 2H, H-3, CH2), 2.93 (t, J=6.7 Hz, 2H, OCH2CH2), 2.82 (m, 1H, CH(CH3)2), 1.16 (d, J=6.8 Hz, 6H, CH(CH3)2). MS-EI 295 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 81

41
[ 66497-42-5 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-(3-hydroxy-6-methyl-pyridin-2-ylmethylene)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyrrolidine; In ethanol; at 90℃; for 4h;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (51 mg, 0.3 mmol), 3-hydroxy-6-methyl-pyridine-2-carbaldehyde (45 mg, 0.33 mmol) and 1 drop of pyrrolidine in 2.0 mL of ethanol was heated at 90 C. for 4 hours and cooled to room temperature. The precipitate was filtered, washed with cold ethanol and hexane, and dried in a vacuum oven overnight to give mixture of isomers of 4-(2-hydroxy-ethyl)-3-(3-hydroxy-6-methyl-pyridin-2-ylmethylene)-1,3-dihydro-indol-2-one. MS-EI 296 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 94-95

42
[ 295800-15-6 ]
[ 139122-19-3 ]
3-[4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyrrolidine; In ethanol; at 90℃; for 4h;Heating / reflux;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (177 mg, 1.0 mmol), 4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde (208 mg, 1.0 mmol) and 3 drops of pyrrolidine in 2.0 mL of ethanol was refluxed at 90 C. for 4 hours and cooled to room temperature. The precipitate was filtered, washed with cold ethanol and hexane, and dried in a vacuum oven overnight to give 360.6 mg (98%) of 3-[4-(3-dimethylamino-propyl)-3,5-dimethyl-1H-pyrrol-2-ylmethylene]-4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one. 1H-NMR (300 MHz, DMSO-d6) delta 13.47 (s, br, 1H, NH), 10.79 (s, br, 1H, NH), 7.56 (s, 1H, H-vinyl), 6.99 (m, 1H, Ar-H), 6.76 (m, 2H, Ar-H), 4.9 (s, br, 1H, OH), 3.7 (m, 2H, CH2), 3.07 (m, 2H, CH2), 2.93 (m, 2H, CH2), 2.67 (s, 6H, 2*CH3), 2.42 (m, 2H, CH2), 2.29 (s, 3H, CH3), 2.20 (s, 3H, CH3), 1.73 (m, 2H, CH2).

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 87

43
[ 1196-69-6 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-(1H-indol-5-ylmethylene)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With piperidine; In ethanol; at 90℃;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (39 mg, 0.22 mmol), 1H-indole-5-carbaldehyde (32 mg, 0.22 mmol) and 1 drop of piperidine in ethanol was heated at 90 C. for overnight and cooled to room temperature. The reaction mixture was concentrated and the residue was purified on silica gel column to give 48 mg (72%) of 4-(2-hydroxy-ethyl)-3-(1H-indol-5-ylmethylene)-1,3-dihydro-indol-2-one as a yellow solid. 1H-NMR (360 MHz, DMSO-d6) 11.28 (s, br, 1H, NH), 10.48 (s, br, 1H, NH), 8.59 (s, 1H), 8.06 (d, 1H), 7.89 (s, 1H, H-vinyl), 7.4 (m, 2H), 7.06 (t, J=7 Hz, 1H, H-6), 6.09 (d, J=7 Hz, 1H, H-5), 6.68 (d, J=7 Hz, 1H, H-7), 6.53 (s, 1H), 4.86 (t, 1H, OH), 3.75 (m, 2H, -CH2CH2OH), 3.11 (m, 2H, -CH2CH2OH). MS-EI 304 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 84-85

44
[ 258831-62-8 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-(4-methoxy-3-thiophen-2-yl-benzylidene)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With piperidine; In ethanol;Heating / reflux;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.6 g, 9.2 mmol), 4-methoxy-3-thiophen-2-yl-benzaldehyde (2 g, 9.2 mmol) and piperidine (4.5 mL, 85 mmol) in ethanol (46 mL) was heated to reflux for overnight. The reaction mixture was concentrated and the residue was chromatographed on a column of silica gel to give 1.63 g (47%) of 4-(2-hydroxy-ethyl)-3-(4-methoxy-3-thiophen-2-yl-benzylidene)-1,3-dihydro-indol-2-one as a yellow orange solid. 1H-NMR (300 MHz, DMSO-d6) delta 10.53 (s, br, 1H, NH), 8.73 (d, J=2.1 Hz, 1H), 8.10 (dd, J=2.2 & 9.1 Hz, 1H), 7.74 (s, 1H, H-vinyl), 7.56-7.65 (m, 2H), 7.07-7.22 (m, 3H), 6.81 (d, J=7.5 Hz, 1H), 6.68 (dd, J=0.6, 7.5 Hz, 1H), 4.87 (t, J=4.5 Hz, 1H, OH), 3.97 (s, 3H, OCH3), 3.68-3.75 (m, 2H, CH2CH2OH), 3.09 (t, J=4.5 Hz, 2H, CH2CH2OH). MS-EI 377 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 85

45
[ 1122-72-1 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-(6-methyl-pyridin-2-ylmethylene)-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; In ethanol; at 100℃; for 1h;	A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (89 mg, 0.5 mmol), 6-methyl-2-pyridine-carbaldehyde (61 mg, 0.5 mmol) and piperidine (0.1 mL) in 1.0 mL of ethanol was heated at 100 C. for 1 hour and cooled to room temperature. The precipitate was filtered and recrystallized from ethyl acetate and hexanes to give 4-(2-hydroxy-ethyl)-3-(6-methyl-pyridin-2-ylmethylene)-1,3-dihydro-indol-2-one as a yellow solid. [00704] 1HNMR (360 MHz, DMSO-d6) delta 10.53 (s, 1H, NH), 8.18 (d, J=7.5 Hz, 1H), 7.68 (t, J=7.5 Hz, 1H), 7.64 (s, 1H), 7.19 (d, J=7.5 Hz, 1H), 7.14 (t, J=7.5 Hz, 1H), 6.82 (d, J=7.5 Hz, 1H), 6.68 (m, 1H), 4.78 (t, J=5 Hz, 1H, OH), 3.68-3.74 (m, 2H, CH2CH2OH), 3.02 (t, J=7 Hz, 2H, CH2CH2OH), 2.49 (s, 3H, CH3). [00705] MS-EI 280 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 83-84

46
[ 74115-12-1 ]
[ 139122-19-3 ]
4-[2-(5-chloro-pyridin-3-yloxy)-ethyl]-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 48h;	Diethyl azodicarboxylate (1.74 g, 10 mmol) was added to a solution of triphenylphosphine (2.62 g, 10 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere. The mixture was stirred for 15 minutes. To it was then added 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (1.77 g, 10 mmol) followed by 5-chloro-3-pyridinol (1.29 g, 10 mmol). The mixture was stirred at room temperature for 2 days. The precipitate was collected by vacuum filtration, washed with ethyl acetate and dried to give 1.05 g (36%) of 4-[2-(5-chloro-pyridin-3-yloxy)-ethyl]-1,3-dihydro-indol-2-one as a light brown solid. 1H-NMR (360 MHz, DMSO-d6) delta 10.31 (s, br, 1H, NH), 8.23 (d, J=2.3 Hz, 1H, Ar-H), 8.17 (d, J=2.3 Hz, 1H, Ar-H), 7.58 (t, J=2.3 Hz, 1H, Ar-H), 7.11 (t, J=7.9 Hz, 1H, Ar-H), 6.87 (d, J=7.9 Hz, 1H, Ar-H), 6.68 (d, J=7.9 Hz, 1H, Ar-H), 4.30 (t, J=6.9 Hz, 2H, CH2CH2O), 3.51 (s, 2H, CH2, H-3), 2.97 (t, J=6.9 Hz, 2H, CH2CH2O). MS-EI 288 [M]+.

Reference： [1]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 94

47
[ 139122-19-3 ]
[ 358733-32-1 ]

Yield	Reaction Conditions	Operation in experiment
28%	With chlorosulfonic acid; at 20℃; for 0.5h;	Example 1; 6,6-Dioxo-3,6,8,9-tetrahvdro-I H-7 -oxa-6A 6 -thia-3-aza-cvclopentar alnaphthalen-2-one; 4-Hydroxyethyl oxindole (5 g, 28.2 mmol) was dissolved in 20 mL of chlorosulfonic acid with stirring at room temperature. After 30 minutes, the reaction mixture was slowly added to 300 mL of ice water with stirring. The solids were filtered and dried to afford 1.9 g (28 % yield) of 6,6-dioxo- 3,6,8,9-tetrahydro-1 H 7-oxa-6(at),6-thia-3-aza-cyclopenta[a]naphthalen-2-one as a white powder. Rf = 0.62 (10% methanol in dichloromethane).

Reference： [1]Patent: WO2005/113561,2005,A1 .Location in patent: Page/Page column 35

48
[ 251356-81-7 ]
[ 139122-19-3 ]
3-[3,5-Dimethyl-4-(4-Methylpiperazine-1-Carbonyl)-1H-Pyrrol-2-Ylmethylene]-4-(2-Hydroxyethyl)-1,3-Dihydroindol-2-One [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90 mg (55%)		Example 54 Synthesis of 3-[3,5-Dimethyl-4-(4-Methylpiperazine-1-Carbonyl)-1H-Pyrrol-2-Ylmethylene]-4-(2-Hydroxyethyl)-1,3-Dihydroindol-2-One 4-(2-Hydroxyethyl)-1,3-dihydroindol-2-one (71 mg, 0.4 mmol) was condensed with 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde to give 90 mg (55%) of the title compound as an orange solid. 1H-NMR (300 MHz, DMSO-d6) delta 14.25(s, 1H, NH), 10.88 (s, 1H, NH), 7.57 (s, 1H, H-vinyl), 7.03 (m, 1H), 6.75-6.82 (m, 2H), 4.86 (m, 1H, OH), 3.70 (m, 2H, CH2), 3.04 (m, 2H, CH2), 2.48 (m, 4H, 2*CH2), 2.28 (br s, 7H), 2.19 (s, 3H, CH3), 2.18 (s, 3H, CH3). MS m/z (+ve) 4.09.3 [M+].
90 mg (55%)		Example 85 3-[3,5-Dimethyl-4-(4-methylpiperazine-1-carbonyl) -1H-pyrrol-2-ylmethylene]-<strong>[139122-19-3]4-(2-hydroxyethyl)-1,3-dihydroindol-2-one</strong> 4-(2-Hydroxyethyl)-1,3-dihydroindol-2-one (71 mg, 0.4 mmol) was condensed with 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde to give 90 mg (55%) of the title compound as an orange solid. 1H-NMR (300 MHz, DMSO-d6) delta 14.25(s, 1H, NH), 10.88 (s, 1H, NH), 7.57 (s, 1H, H-vinyl), 7.03 (m, 1H), 6.75-6.82 (m, 2H), 4.86 (m, 1H, OH), 3.70 (m, 2H, CH2), 3.04 (m, 2H, CH2), 2.48 (m, 4H, 2*CH2), 2.28 (br s, 7H), 2.19 (s, 3H, CH3), 2.18 (s, 3H, CH3). MS m/z (+ve) 4.09.3 [M+].

Reference： [1]Patent: US2003/100555,2003,A1
[2]Patent: US2002/156292,2002,A1

49
[ 251356-81-7 ]
[ 139122-19-3 ]
3-[3.5-Dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-4-(2-hydroxyethyl)-1,3-dihydroindol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90 mg (55%)		Example 85 3-[3.5-Dimethyl-4-(4-methylpiperazine-1-carbonyl)-1H-pyrrol-2-ylmethylene]-<strong>[139122-19-3]4-(2-hydroxyethyl)-1,3-dihydroindol-2-one</strong> 4-(2-Hydroxyethyl)-1,3-dihydroindol-2-one (71 mg, 0.4 mmol) was condensed with 3,5-dimethyl-4-(4-methyl-piperazine-1-carbonyl)-1H-pyrrole-2-carbaldehyde to give 90 mg (55%) of the title compound as an orange solid. 1H-NMR (300 MHz, DMSO-d6) delta 14.25(s, 1H, NH), 10.88 (s, 1H, NH), 7.57 (s, 1H, H-vinyl), 7.03 (m, 1H), 6.75-6.82 (m, 2H), 4.86 (m, 1H, OH), 3.70 (m, 2H, CH2), 3.04 (m, 2H, CH2), 2.48 (m, 4H, 2*CH2), 2.28 (br s, 7H), 2.19 (s, 3H, CH3), 2.18 (s, 3H, CH3). MS m/z (+ve) 4.09.3 [M+].

Reference： [1]Patent: US2003/216410,2003,A1

50
[ 110-89-4 ]
[ 139122-19-3 ]
[ 358732-55-5 ]
1-[4-(2-hydroxy-ethyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	1-[4-(2-Hydroxy-ethyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (35.4 mg, 0.2 mmol), 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde (32.8 mg, 0.2 mmol) and 0.1 mL of piperidine in ethanol (1 mL) was heated in a sealed tube at 80 C. for 4 hours. The precipitate was collected by vacuum filtration, washed with cold ethanol and dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) delta 13.62 (br s, 1H, NH), 11.0 (s, 1H, NH), 7.66 (d, J=3.0 Hz, 1H), 7.55 (s, 1H, H-vinyl), 7.38 (br s, 1H, NH), 7.07 (t, J=7.6 Hz, 1H), 6.83 (d, J=7.6 Hz, 1H), 6.76 (d, J=7.6 Hz, 1H), 4.89 (t, J=4.7 Hz, 1H, OH), 3.70 (m, 2H, CH2), 3.41 (m, 2H, CH2), 3.06 (t, J=7.2 Hz, 2H, CH2), 2.89 (t, J=6.4 Hz, 2H, CH2). MS m/z 324 [M++1].

Reference： [1]Patent: US2002/42427,2002,A1

51
[ 380240-94-8 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-[5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 41 COMPOUND IN-033 4-(2-Hydroxy-ethyl)-3-[5-(2-morpholin-4-yl-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one 4-(2-Hydroxy-ethyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-morpholin-4-yl-ethoxy)-1HH-indole-2-carbaldehyde to give the title compound.

Reference： [1]Patent: US2002/52369,2002,A1

52
[ 380240-91-5 ]
[ 139122-19-3 ]
4-(2-hydroxy-ethyl)-3-[5-(2-pyrrolidin-1-yl-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 32 COMPOUND IN-024 4-(2-Hydroxy-ethyl)-3-[5-(2-pyrrolidin-1-yl-ethoxy)-1H-indol-2-ylmethylene]-1,3-dihydro-indol-2-one 4-(2-Hydroxy-ethyl)-1,3-dihydro-indol-2-one was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound. 1H-NMR (360 MHz, DMSO-d6) delta 13.03 (s, 1H, NH), 10.98 (br s, 1H, NH), 7.76 (s, 1H, H-vinyl), 7.48 (d, J=9 Hz, 1H), 7.12 (m, 3H), 6.92 (dd, J=2.5 & 9 Hz, 1H), 6.86 (d, J=8 Hz, 1H), 6.77 (d, J=8 Hz, 1H), 4.83 (t, J=5.4 Hz, 2H, OH), 4.07 (t, J=6 Hz, 2H, CH2), 3.74 (m, 2H, CH2), 3.12 (m, 2H, CH2), 2.80 (t, J=6 Hz, 2H, CH2), 2.52 (m, 4H, 2CH2), 1.68 (m, 4H, 2CH2). MS-Ve APCI 416.6. [M+-1].

Reference： [1]Patent: US2002/52369,2002,A1

Yield	Reaction Conditions	Operation in experiment
		E. Preparation of 4-(2'-hydroxyethyl)-1,3-dihydro-2H-indol-2-one. The product from D (10.25 g, 1 equiv.) and solid sodium hydroxide (1.56 g) were stirred in water (50 ml) and methanol (20 ml) and heated to reflux for 2 hours. Methanol was then removed via distillation and the reaction mixture was then cooled. The pH of the reaction mixture was adjusted to 7 and the creamy white precipitate was collected at the pump, washed with water (120 ml) and dried at 80 overnight to give the title compound, 5.56 g, 89%.

54
[ 855382-76-2 ]
[ 139122-19-3 ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 714 - 717
[2]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[3]Patent: CN103130704,2019,B

55
[ 1426679-27-7 ]
[ 139122-19-3 ]

Yield	Reaction Conditions	Operation in experiment
285 g	With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20℃; under 760.051 Torr; for 48h;	The crude compound (VII) obtained in Example 5 and 64 g of 10% palladium carbon were added to 20 L of ethyl acetate, and hydrogen was passed. Subsequently, the reaction was stopped after reacting for 48 hours under normal temperature and normal pressure. Palladium carbon was removed by filtration, and the solvent was evaporated under reduced pressure. When about 10% of the solvent remained, the distillation was stopped, allowed to stand, and solids were precipitated. The solid was filtered, washed with ethyl acetate and dried. There was obtained 285 g of 4-(2-hydroxyethyl)-1,3-dihydro-2H-indol-2-one (I) as a white solid, purity 99%, with a total yield of 62.5%.

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[2]Organic Process Research and Development,2013,vol. 17,p. 714 - 717
[3]Patent: CN103130704,2019,B .Location in patent: Paragraph 0060; 0061

56
[ 23876-15-5 ]
[ 139122-19-3 ]

Reference： [1]Organic Process Research and Development,2013,vol. 17,p. 714 - 717
[2]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[3]Patent: CN103130704,2019,B

57
[ 139122-19-3 ]
N-Despropylropinirole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[2]MedChemComm,2014,vol. 5,p. 891 - 898
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738
[4]Patent: CN105461608,2016,A
[5]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609

58
[ 139122-19-3 ]
4-ethylenyl-1,3-dihydro-2H-indol-2-one [ No CAS ]
N-Despropylropinirole [ No CAS ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144

59
[ 139122-19-3 ]
[ 120427-96-5 ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144

60
[ 1426679-26-6 ]
[ 139122-19-3 ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[2]Patent: CN103130704,2019,B

61
[ 1441070-77-4 ]
[ 139122-19-3 ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144

62
[ 139122-16-0 ]
[ 139122-19-3 ]

Reference： [1]Monatshefte fur Chemie,2014,vol. 145,p. 1139 - 1144
[2]Patent: CN105461608,2016,A
[3]Patent: CN105418482,2016,A
[4]Chemical Biology and Drug Design,2018,vol. 92,p. 1597 - 1609

63
[ 139122-19-3 ]
[ 1632235-97-2 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738
[4]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738

64
[ 139122-19-3 ]
[ 1632166-05-2 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

65
[ 139122-19-3 ]
[ 1632166-06-3 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

66
[ 139122-19-3 ]
[ 1632166-07-4 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

67
[ 139122-19-3 ]
[ 1632166-08-5 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

68
[ 139122-19-3 ]
[ 1632166-09-6 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

69
[ 139122-19-3 ]
[ 1632166-10-9 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898

70
[ 139122-19-3 ]
4-<2-(N-propylamino)ethyl>-2-indolone hydrochloride [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738

71
[ 139122-19-3 ]
ethyl 4-(N-propyl-<2-<4-(2-oxy-3H-indolyl)>>ethylamino)butanoate [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898

72
[ 139122-19-3 ]
[ 1632166-02-9 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 891 - 898
[2]MedChemComm,2014,vol. 5,p. 891 - 898
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 718 - 738

73
[ 139122-19-3 ]
tert-butyl (4-oxo-4-((3-((2-(2-oxoindolin-4-yl)ethyl)(propyl)amino)propyl)amino)butyl)carbamate [ No CAS ]