85926-99-4|Indolin-4-ol| Ambeed

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Quality Control of [ 85926-99-4 ] Purity: 98% SDS Specification

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Product Details of [ 85926-99-4 ]

CAS No. :	85926-99-4
Formula :	C₈H₉NO
M.W :	135.16
SMILES Code :	OC1=CC=CC2=C1CCN2
MDL No. :	MFCD09056797
InChI Key :	OWWAUBQOFLVUMS-UHFFFAOYSA-N
Pubchem ID :	3021054

Safety of [ 85926-99-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P305+P351+P338

Application In Synthesis of [ 85926-99-4 ]

* 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.

Downstream synthetic route of [ 85926-99-4 ]

[ 85926-99-4 ] Synthesis Path-Downstream 1~41

1
[ 496-15-1 ]
[ 4770-37-0 ]
[ 85926-99-4 ]

References: [1]Tetrahedron Letters,1986,vol. 27,p. 4565 - 4568.

2
[ 85926-99-4 ]
[ 2380-94-1 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

3
[ 52537-01-6 ]
[ 85926-99-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

4
[ 118742-89-5 ]
[ 85926-99-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

5
[ 118742-89-5 ]
[ 85926-99-4 ]
[ 52537-01-6 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

6
[ 606-20-2 ]
[ 85926-99-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

7
[ 77759-08-1 ]
[ 85926-99-4 ]

References: [1]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 3742 - 3744.

8
[ 2380-94-1 ]
[ 85926-99-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		Synthesis of CDNI-GAB A.; [0068] Synthesis of compound 2b.; 4-Acetoxy-l-acetylindoline. A solution of 4-hydroxyindole (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at <15 C. The mixture was then stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6.76 g. 100%); IH NMR (δ, CDCl3 DMSO-J6): 6.82 (IH, t, J= 8 Hz), 6.20 (IH, d, J= 8 Hz), 6.16 (IH, d, J= 8 Hz), 3.52 (2H, t, J= 8 Hz) and 2.90 (2H, d, J= 8 Hz). The crude indoline was dissolved in a mixture of acetic acid (50 mL) and acetic anhydride (50 mL) and heated under reflux for 1 h. The solution was diluted with water (10 mL) and the solvents evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4-acetoxy-l- acetylindoline as pale crystals (9.01 g, 82%), NMR (δ, 90 MHz): 8.07 (IH, d, J= 8 Hz), 7.19 (IH, t, J= 8 Hz), 6.72 (IH, d, J= 8 Hz), 4.05 (2H, t, J= 8 Hz), 3.03 (2H, t, J= 8 Hz) 2.28 (3H, s) and 2.19 (3H, s).
100%	With sodium cyanotrihydridoborate; In glacial acetic acid; at 15 - 20℃; for 1.5h;	A solution of 4-hydroxyindole 26 (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at-15oC. The mixture was stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NAHC03 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6. 76 g. 100%) ; 1H NMR: (90 MHz, CDC13 + DMSO-d6) # 6. 82 (1H, t, J = 8 Hz), 6.20 (1H, d, J = 8 Hz), 6.16 (1H, d, J = 8 Hz), 3.52 (2H, t, J = 8 Hz) and 2.90 (2H, d, J = 8 Hz).
99%	With sodium cyanotrihydridoborate; In glacial acetic acid; at 15 - 20℃;	A solution of 4-hydroxyindole (0.16 g; 1.2 mmol) in AcOH (6 ml) was treated with NaBH3CN (0.23 g; 3.6 mmol), at rate keeping the temperature below 150C. The mixture was then stirred for 1 h at room temperature and H2O (0.4 ml) was added and solvents removed in vacuo. The residue was diluted to 15 ml with EtOAc, washed with 5% NaHCO3, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated under reduced pressure to give the title compound (0.16 g; 99%) as creamy solid. 1 H-NMR (CDCI3 ) 2.93 (tr, 2H, J = 8.4 Hz); 3.58 (tr, 2H, J = 8.4 Hz); 3.74 (broad S, 2H); 6.17 (d, 1 H, J = 8 Hz); 6.26 (d, 1 H, J = 7.72 Hz); 6.88 (tr, 1 H, J = 7.85 Hz).

92%	With sodium cyanotrihydridoborate; glacial acetic acid; at 0 - 20℃; for 1h;	Take 2.12 g of 4-hydroxyindole into a 100 mL flask, add 30 mL of glacial acetic acid, and stir under ice bath. Weigh 1.51 g of sodium cyanoborohydride into a small Erlenmeyer flask and stopper. Then add sodium cyanoborohydride to a small amount of batchwise mixture. After stirring for 1 hour at room temperature, add 5mL deionized water and stir for 10min, remove acetic acid under reduced pressure, pour into 100mL:200mL ethyl acetate and water mixture, add 1.8g sodium bicarbonate, stir until no bubbles are generated, extract and separate The organic phase was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was decompressed to remove the solvent to obtain 1.98 g of solid, with a yield of 92%. The hydrogen spectrum data of the NMR spectrum are as follows:
66.99%	With sodium cyanotrihydridoborate; glacial acetic acid; at 0 - 20℃; for 0.5h;	At room temperature, 1H-indol-4-ol (10 g) was dissolved in AcOH (30 ml), and after cooling in an ice bath, sodium cyanoborohydride (11.80 g) was added in batches, and the temperature was controlled below 15C for 0.5 reaction h. Ice water was added to quench the reaction, saturated aqueous sodium carbonate solution was adjusted to neutral pH, extracted twice with EA (300ml*2), the organic phases were combined, washed with saturated brine, and concentrated. The concentrate was separated and purified by silica gel column (DCM:MeOH=99:1-30:1) to obtain white-green product 1-1 (6.8 g, yield 66.99%).
59%	With sodium cyanotrihydridoborate; In glacial acetic acid; at 0 - 20℃; for 3h;Inert atmosphere;	General procedure: NaBH(CN)3 (1.4 g, 22.60 mmol) was added slowly to a solution of 8 (1.0 g, 7.51 mmol) in AcOH (20 mL) at 0, and then the mixture was stirred for 3 h at room temperature under N2 atmosphere. The resulting reaction mixture was quenched with saturated NH4Cl solution (3 mL) and concentrated under reduced pressure to give the residue, which was redissolved in EtOAc (50 mL), and washed with saturated NaHCO3 (50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (5:1-3:1-2:1, v/v) to provide the intermediate 9 (0.61 g, 60% yield) as a brown solid.

References: [1]Patent: WO2008/94922,2008,A1 .Location in patent: Page/Page column 19.
[2]Patent: WO2004/85394,2004,A1 .Location in patent: Page 24-25.
[3]Patent: WO2010/42998,2010,A1 .Location in patent: Page/Page column 102.
[4]Patent: CN111333660,2020,A .Location in patent: Paragraph 0032-0037; 0051-0055.
[5]Patent: CN113979995,2022,A .Location in patent: Paragraph 0067-0070; 0140-0143.
[6]European Journal of Medicinal Chemistry,2018,vol. 157,p. 380 - 396.
[7]Journal of Medicinal Chemistry,2012,vol. 55,p. 10700 - 10715.
[8]New Journal of Chemistry,2008,vol. 32,p. 1027 - 1037.

9
[ 85926-99-4 ]
4-acetoxy-1-acetylindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With acetic anhydride; acetic acid; for 1h;Heating / reflux;	A solution of 4-hydroxyindole 26 (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at-15oC. The mixture was stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NAHC03 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6. 76 g. 100%) ; 1H NMR: (90 MHz, CDC13 + DMSO-d6) # 6. 82 (1H, t, J = 8 Hz), 6.20 (1H, d, J = 8 Hz), 6.16 (1H, d, J = 8 Hz), 3.52 (2H, t, J = 8 Hz) and 2.90 (2H, d, J = 8 Hz). The crude indoline was dissolved in a mixture of acetic acid (50 ML) and acetic anhydride (50 mL) and heated under reflux for 1 h. The solution was diluted with water (10 ML) and the solvents evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NAHCO3 and brine, dried and evaporated to give 27 as pale crystals (9.01 g, 82%), mp 98-99oC (EtOAc-petroleum ether); (Found: C, 65.56 ; H, 6.07 ; N, 6. 39 ; CALCD. for C12HL3NO3 : C, 65.74 ; H, 5.98 ; N, 6. 39%) ; IR: V.,,,/CM- 1755, 1635,1610, 1215 ; 1H NMR: (90 MHz) # 8.07 (1H, d, J = 8 Hz), 7.19 (1H, t, J = 8 Hz), 6.72 (1H, d, J = 8 Hz), 4.05 (2H, t, J = 8 Hz), 3.03 (2H, t, J = 8 Hz) 2. 28 (3H, s) and 2. 19 (3H, s).

References: [1]Patent: WO2004/85394,2004,A1 .Location in patent: Page 24-25.

10
[ 108-24-7 ]
[ 85926-99-4 ]
[ 64-19-7 ]
4-acetoxy-1-acetylindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Synthesis of CDNI-GAB A.; [0068] Synthesis of compound 2b.; 4-Acetoxy-l-acetylindoline. A solution of 4-hydroxyindole (6.66 g, 50 mmol) in acetic acid (250 mL) was treated with NaBH3CN (9.42 g, 150 mmol) over 0.5 h, keeping the temperature at <15 C. The mixture was then stirred at room temperature for 1 h and water (5 mL) was added and the solvent evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4- hydroxyindoline as pale crystals (6.76 g. 100%); IH NMR (δ, CDCl3 DMSO-J6): 6.82 (IH, t, J= 8 Hz), 6.20 (IH, d, J= 8 Hz), 6.16 (IH, d, J= 8 Hz), 3.52 (2H, t, J= 8 Hz) and 2.90 (2H, d, J= 8 Hz). The crude indoline was dissolved in a mixture of acetic acid (50 mL) and acetic anhydride (50 mL) and heated under reflux for 1 h. The solution was diluted with water (10 mL) and the solvents evaporated. The residue was dissolved in EtOAc (150 mL) and washed with saturated aq. NaHCO3 and brine, dried and evaporated to give 4-acetoxy-l- acetylindoline as pale crystals (9.01 g, 82%), NMR (δ, 90 MHz): 8.07 (IH, d, J= 8 Hz), 7.19 (IH, t, J= 8 Hz), 6.72 (IH, d, J= 8 Hz), 4.05 (2H, t, J= 8 Hz), 3.03 (2H, t, J= 8 Hz) 2.28 (3H, s) and 2.19 (3H, s).

References: [1]Patent: WO2008/94922,2008,A1 .Location in patent: Page/Page column 19.

11
[ 85926-99-4 ]
[ 407-25-0 ]
[ 1221259-92-2 ]

Yield	Reaction Conditions	Operation in experiment
31%	With pyridine; at 0 - 20℃;Inert atmosphere;	To a solution of the product of Example 41 , Step A (0.31 g; 2.25 mmol) in anhydrous pyridine, (CF3CO)2O (0.35 ml; 2.5 ml) was added drop wise at O0C with stirring under N2. After stirring for 30 min at room temperature solvents were removed in vacuo and the residue was diluted to 20 ml with EtOAc, washed with diluted HCI (2 x 5 ml), brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2, CH2CI2 : EtOAc, 8 : 2) to give the title compound (0.16 g; 31 %), as colourless solid. 1H-NMR (CDCI3) 3.19 (tr, 2H, J = 8.2 Hz); 4.28 (tr, 2H, 8 Hz); 5.17 (s, 1 H); 6.61 (d, 1 H, J = 8.1 Hz); 7.13 (tr, 1 H, J = 8.1 Hz); 7.78 (d, 1 H, J = 8.1 Hz).

References: [1]Patent: WO2010/42998,2010,A1 .Location in patent: Page/Page column 146.

12
[ 85926-99-4 ]
[ 107-99-3 ]
[ 847460-38-2 ]

Yield	Reaction Conditions	Operation in experiment
51%		In a 3:1 mixture of 200 ml of toluene and methanol 6.6g (0.123 mole) of sodium methylate were dissolved, then a solution of 15 g of (0.1125 mole) 4- hydroxyindole in 250 ml of a 3:2 mixture of toluene and methanol at 60 C was added dropwise to the solution, then the mixture was stirred for half an hour at this temperature. Then 14.5g (0.135 mole) dimethyl-amino-ethylchloride were dissolved in 14.5m1 of toluene at 60 C and stirred for further 5 hours at this temperature. During this time the 4-hydroxy-indol completely transformed. Then 300 ml of ethyl acetate were added to the reaction mixture, then the mixture was filtered through Perlite. The solution was extracted with saturated sodium hydrogen carbonate solution, following the separation it was extracted with 3x150 ml of water, dried on magnesium sulphate, then evaporated.The product thus given is 10.82g (51%) pale brown oil of 4-dimethylamino- ethoxy-indole (DMEO-lndole)

References: [1]Patent: WO2013/50795,2013,A1 .Location in patent: Page/Page column 22.

13
[ 85926-99-4 ]
[ 1429743-47-4 ]

References: [1]Patent: WO2013/50795,2013,A1 .

14
[ 85926-99-4 ]
[ 1429660-63-8 ]

References: [1]Patent: WO2013/50795,2013,A1 .

15
[ 85926-99-4 ]
4-amino-1-(4-(2-dimethylamino)ethoxy-2,3-dihydroindol-1-yl)-1-oxobutane di-trifluoroacetic acid [ No CAS ]

References: [1]Patent: WO2013/50795,2013,A1 .

16
[ 85926-99-4 ]
4-amino-1-(4-(2-dimethylamino)ethoxy-5,7-dinitro-2,3-dihydroindol-1-yl)-1-oxobutane di-trifluoroacetic acid [ No CAS ]

References: [1]Patent: WO2013/50795,2013,A1 .

17
[ 85926-99-4 ]
[ 98-59-9 ]
[ 1452925-60-8 ]