15861-23-1|Indoline-5-carbonitrile| Ambeed

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Quality Control of [ 15861-23-1 ] Purity: 97% SDS Specification

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Product Details of [ 15861-23-1 ]

CAS No. :	15861-23-1
Formula :	C₉H₈N₂
M.W :	144.17
SMILES Code :	N#CC1=CC2=C(NCC2)C=C1
MDL No. :	MFCD07371626
InChI Key :	KBNWGVBBEPQFIZ-UHFFFAOYSA-N
Pubchem ID :	21907639

Safety of [ 15861-23-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Application In Synthesis of [ 15861-23-1 ]

* 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 [ 15861-23-1 ]

[ 15861-23-1 ] Synthesis Path-Downstream 1~35

3
[ 15861-24-2 ]
[ 15861-23-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylsilane; In trifluoroacetic acid; at 0℃; for 4h;	A solution of 5-cyanoindole (1 g, 7 mmol) in 10 mL TFA was cooled to 0 C. and then triethylsilane (1.6 g, 2 eq.) was added. The reaction mixture was stirred at 0 C. for 4 h then diluted with EtOAc and washed with 1M HCl solution. The aqueous layers were combined and neutralized with 50% NaOH to pH10 then extracted 3× with EtOAc. These latter extracts were combined, washed with brine, dried and evaporated to yield the indoline (77%).
67%	With boron trifluoride diethyl etherate; sodium cyanoborohydride; In methanol; at 25℃;	Dissolve 5-cyanoindole (142 mg, 1 mmol) and sodium cyanoborohydride (63 mg, 1 mmol) in methanol (2 ml). Boron trifluoride etherate (152 drops, 1.2 mmol) was added dropwise and allowed to react at room temperature for 2-3 hours. After quenching, add 25% ammonia to quench. The reaction was followed by extraction with ethyl acetate (10 mL x 3 times). The organic layers were combined, dried over anhydrous magnesium sulfate, concentrated and subjected to column chromatography (oilEther: ethyl acetate = 10:1) was isolated to give 97 mg of the desired product in 67% yield.
56%	With triethylsilane; trifluoroacetic acid; at 0 - 20℃; for 2h;	Triethylsilane (2.0 eq.) was slowly added to a solution of indole (1 .0 eq.) in trifluoroacetic acid (1 .4 M), cooled to 0 C. The reaction mixture was stirred at 0 C for 1 h, then at r.t. for 1 h. Upon completion (monitored by TLC), the reaction was basified to pH 1 1 with NaOH (5.0 M) and extracted with EtOAc (x3). The organic layers were combined, washed with brine, dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by flash chromatography to give the desired indoline. Following general procedure M, 5-cyanoindole (600.0 mg, 4.22 mmol) afforded indoline-5-carbonitrile (340.0 mg, 2.36 mmol, 56% yield) as a light yellow solid. UPLC-MS (ES+, Short acidic): 1 .30 min, m/z 289.0 [2M+H]+.

40%	With sodium cyanoborohydride; In acetic acid; at 20℃;	A solution of 5-cyanoindole (3 g, 0.021 mol) in glacial acetic acid (25 mL) was treated portionwise with sodium cyanoborohydride (4 g, 0.063 mol) over 20-30 min then the solution was stirred overnight at rt under N2. The reaction was quenched by addition of water, and most of acetic acid was removed in vacuo. The residue was diluted with water and adjusted to pH>8 with 1M NaOH then extracted 3× with ethyl acetate. Extracts were combined and back extracted 2× with 1M HCl then set aside. (Starting indole can be recovered from these initial EtOAc extracts if desired.) Aqueous acid extracts were combined and rebasified with 5N NaOH, and then re-extracted with EtOAc. The latter extracts were combined, washed with brine, dried over anh. Na2SO4, filtered and evaporated to provide the indoline product (1.22 g, 40%) as an off-white crystalline solid. 1H NMR (CDCl3, 300 MHz) delta 7.29-7.31 (m, 2H), 6.54 (d, 1H, J=8.4 Hz), 4.20 (bs, 1H), 3.67 (t, 2H, J=8.6 Hz), 3.06 (t, 2H, J=8.6 Hz)
33%		Reference Example 7 2,3-dihydro-1H-indole-5-carbonitrile; To a solution (5 mL) cooled to 0C in an ice bath of 1H-indole-5-carbonitrile (640 mg, 4.50 mmol) in acetic acid was added sodium cyanotrihydroborate (848 mg, 13.5 mmol). The reaction mixture was stirred at room temperature for 5 hr and diluted with water. The mixture was basified with 8N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid and the aqueous layer was again basified with 8N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated. The residue was crystallization from ethyl acetate to give the title compound as pale-yellow crystals (213 mg, yield 33%). 1H-NMR (300 MHz, CDCl3)delta:3.06 (t, J = 8.5 Hz, 2 H), 3.67 (t, J = 8.7 Hz, 2 H), 3.83 (br s, 1 H), 6.45 - 6.59 (m, 1 H), 7.24 - 7.33 (m, 2 H).
	With triethylsilane; In trifluoroacetic acid; at 0℃; for 4h;	To a stirred solution of 5-cyanoindole (20.0 g, 140 mmol) in trifluoroacetic acid (150 mL) at 0 C. was added triethylsilane (45.2 mL, 281 mmol). The reaction mixture was stirred for 4 h at 0 C. The reaction mixture was diluted with EtOAc (200 mL) and the organic layer was extracted with 1N HCl (200 mL). The aqueous layer was basified with 50% NaOH solution to pH 10-11 and extracted with EtOAc (2*200 mL). The combined organic layers were dried over anhydrous Na2SO4 and evaporated to dryness to give 2,3-dihydro-1H-indole-5-carbonitrile (6.2 g, 31%) as a pale yellow solid. The material was used without further purification.

References: [1]Patent: US2004/220206,2004,A1 .Location in patent: Page 25-26.
[2]Journal of Materials Chemistry A,2015,vol. 3,p. 17704 - 17712.
[3]Patent: CN105085504,2018,B .Location in patent: Paragraph 0139; 0147-0150.
[4]Patent: WO2014/188173,2014,A1 .Location in patent: Paragraph 00239; 00521.
[5]Patent: US2004/220206,2004,A1 .Location in patent: Page 25.
[6]Patent: EP2399914,2011,A1 .Location in patent: Page/Page column 92.
[7]Patent: US2012/252853,2012,A1 .Location in patent: Page/Page column 22.

4
[ 762254-20-6 ]
[ 15861-23-1 ]
C₃₅H₃₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃;	A mixture of the compound of Part D (0.3 g, 0.72 mol) and <strong>[15861-23-1]5-cyanoindoline</strong> (0.1 g, 0.694 mmol) in 2.5 mL 1,2-dichloroethane was stirred under N2 for 10 min, followed by the addition of sodium triacetoxyborohydride (0.22 g, 1.04 mmol, 1.5 eq.). The mixture was then stirred overnight at rt. The reaction was quenched by addition of water and 1M NaOH and extracted 3× with CH2Cl2. Extracts were combined, washed with brine and dried over anh. Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 75:25) provided the desired alkylated product as a white foam (120 mg, 32%). 1HNMR (300 MHz, CDCl3) delta 8.27 (s, 1H); 7.93 (d, 1H); 7.30 (6H, m); 7.13-7.02 (6H, m); 6.18 (1H, bt), 5.88 (d, 1H, J=6 Hz); 5.03 (2H, dd, J=18, 10.8); 3.96, (s, 2H); 3.32 (t, 2H, J=6 Hz); 2.81 (t, 2H, J=6 Hz); 1.92 (m, 1H); 1.00 (6H, d, J=6.6 Hz). MS m/z 544.3 (M+H)+.

References: [1]Patent: US2004/220206,2004,A1 .Location in patent: Page 27.

5
[ 16231-67-7 ]
[ 15861-23-1 ]
C₂₄H₂₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃;	The compound of Part A (0.1 g, 0.694 mmol) was dissolved in 1,2-dichloroethane (DCE) (2.5 mL) and a solution of the compound of Part B (80 mg, 0.33 mmol) in DCE (1.5 mL) was added. This mixture was stirred for 10-15 min, then treated with sodium triacetoxyborohydride (0.1 g, 0.48 mmol) and stirred overnight at rt under N2. Reaction was quenched by addition of water and 1N NaOH, then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 4:1) provided the product (0.105 g, 86%). 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, 1H, J=7.5 Hz), 7.50-(t, 1H, J=7.5 Hz), 7.41 (t, 1H, J=7.5 Hz), 7.34-7.30 (m, 2H), 7.23-7.11 (m, 4H), 5.99 (d, 1H, J=8.4 Hz), 4.08 (dd, 2H, J=24.2, 15.8 Hz), 3.59 (s, 3H), 3.33 (m, 2H), 2.91 (t, 2H, J=8.4 Hz). LRMS m/z 369.0 (M+H)+ (API+). HRMS Calcd. for C24H21N2O2: 369.1603. Found: 369.1580.

References: [1]Patent: US2004/220206,2004,A1 .Location in patent: Page 26.

6
[ 787631-44-1 ]
[ 15861-23-1 ]
C₂₇H₂₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃;	A mixture of <strong>[15861-23-1]5-cyanoindoline</strong> (70 mg, 0.487 mmol) and 2'-formylbiphenyl-2,4-dicarboxylic acid 4-ethyl ester 2-methyl ester (0.512 mmol) in 4 mL DCE was stirred for 10 min followed by addition of sodium triacetoxyborohydride (0.155 g, 1.5 eq.). Stirring was continued at rt overnight under N2. Reaction was quenched by addition of 1M NaOH then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over anh. Na2SO4, filtered and evaporated. Flash silica gel chromatography (hexane/ethyl acetate 85:15) provided the product (0.164 g, 76%) as a white, sticky foam. 1H NMR (CDCl3, 300 mHz) delta 8.58 (s, 1H), 8.14 (d, 1H, J=8.4 Hz), 7.36-7.30 (m, 4H), 7.18-7.13 (m, 4H), 6.00 (d, 1H, J=8.4 Hz), 4.44 (q, 2H, J=7.3 Hz), 4.07 (m, 2H), 3.64 (s, 3H), 3.29 (m, 2H), 2.90 (m, 2H), 1.44 (t, 3H, J=7.3 Hz). LRMS (API+) m/z 441.2 (M+H)+ [100].

References: [1]Patent: US2004/220206,2004,A1 .Location in patent: Page 26.

7
[ 787631-65-6 ]
[ 15861-23-1 ]
C₂₄H₁₉N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20℃;	To a solution of <strong>[15861-23-1]5-cyanoindoline</strong> (0.5 g, 3.47 mmol) and the compound of Part D (1.3 g, 1.1 eq.) in 10 mL of DMF was added sodium hydride (60% in oil, 0.15 g, 1.1 eq.). The mixture was stirred overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with water and brine and then dried over Na2SO4, filtered and evaporated. Flash chromatography on silica gel (hexane/CH2Cl2/EtOH 20/80/0.5) provided the desired alkylated product (0.44 g, 31%, MS m/z 414.2 (M+H)+) along with 68% of unreacted starting material.

References: [1]Patent: US2004/220206,2004,A1 .Location in patent: Page 30.

8
[ 7623-09-8 ]
[ 15861-23-1 ]
[ 872045-62-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N,N-dimethyl-aniline; In dichloromethane; at 0℃; for 3h;	To a solution of 2,3-dihydro-lH-indole-5-carbonitrile (8 g, 0.0556 mol; see step (iv) above) in DCM (50 mL) at 0C was added NN-dimethylaniline (13.5 g, 0.1112 mol) followed by 2-chloropropionyl chloride (8.46 g, 0.0667 mol). The reaction mixture was stirred for 3 h before being diluted with water and extracted with DCM. The organic layer was washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel to yield the sub-title compound as a pale yellow solid. Yield: 10.5 g.

References: [1]Patent: WO2005/123748,2005,A1 .Location in patent: Page/Page column 71-72.

9
[ 872045-61-9 ]
[ 15861-23-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 5h;	2,3-Dihydro-lH-indole-5-carbonitrile 1-(2,2,2-Trifluoroacetyl)-2,3-dihydro-lH-indole-5-carbonitrile (13 g, 0.0542 mol; see step (iii) above) was dissolved in THF (100 mL), to which 1 % NaOH was then added. After stirring for 5 h at RT, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and solvent was evaporated to provide the sub-title compound as a pale yellow solid. Yield: 8 g.

References: [1]Patent: WO2005/123748,2005,A1 .Location in patent: Page/Page column 71.

10
[ 15861-23-1 ]
N'-hydroxyindoline-5-carboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine; In water; at 60℃;	To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (0.6 g, 4.2 mmol) was added 50% aqueous hydroxylamine (0.275 g, 8.4 mmol). The reaction mixture was sealed and stirred overnight at 60 0C. After removal of the volatile solvent, the title compound was obtained (0.6 g) without further purification. LCMS m/z = 178.2 [M+H]+.

References: [1]Patent: WO2009/151621,2009,A1 .Location in patent: Page/Page column 50.

11
[ 871681-64-0 ]
[ 15861-23-1 ]
[ 1254361-05-1 ]

Yield	Reaction Conditions	Operation in experiment
61%		A mixture of 4-(6-chloro-pyrimidin-4-yloxy)-piperidine-1 -carboxylic acid isopropyl ester (50.4 mg, 0.168 mmol) and 2,3-dihydro-1 H-indole-5-carbonitrile (22.0 mg, 0.15 mmol) in anhydrous 1 ,4-dioxane (2.0 ml.) was heated to 105 degrees Celsius. After stirring for 5 min, a 1 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (0.184 ml_, 0.184 mmol) was added. After 30 minutes, the reaction mixture was quenched with saturated aqueous ammonium chloride and concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The aqueous phase was extracted three times with dichloromethane, and the combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the crude residue was purified by column chromatography (20-60% ethyl acetate in heptane) to afford isopropyl 4-[6-(5-cyano-2,3-dihydro-1 H-indol-1 -yl)pyrimidin-4-yl]oxy}piperidine-1 - carboxylate (38 mg, 61 %) as a white solid. 1H NMR (400 MHz, deuterochloroform) delta 1.25 (d, J=6.25 Hz, 6 H) 1.68 - 1.78 (m, 2 H) 1.96 - 2.04 (m, 2 H) 3.24 - 3.36 (m, 4 H) 3.78 - 3.87 (m, 2 H) 4.03 (t, J=8.79 Hz, 2 H) 4.89 - 4.97 (m, 1 H) 5.29 - 5.36 (m, 1 H) 5.96 (s, 1 H) 7.43 (s, 1 H) 7.51 (dd, J=8.79, 1.17 Hz, 1 H) 8.48 - 8.53 (m, 2 H). LCMS (ES+): 408.4 (M+1 ).

References: [1]Patent: WO2010/128414,2010,A1 .Location in patent: Page/Page column 91-92.

12
[ 15026-17-2 ]
[ 15861-23-1 ]
tert-butyl 4-(5-cyanoindolin-1-yl)-4-oxobutanoate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6013 - 6018.

13
[ 15026-17-2 ]
[ 15861-23-1 ]
C₁₇H₂₃N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6013 - 6018.

14
[ 24424-99-5 ]
[ 15861-23-1 ]
[ 874841-30-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6013 - 6018.

15
[ 24424-99-5 ]
[ 15861-23-1 ]
tert-butyl 5-(N'-hydroxycarbamimidoyl)indoline-1-carboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6013 - 6018.

16
[ 15861-23-1 ]
[ 101385-93-7 ]
[ 1360095-67-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (1 10 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.1 1 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.
		Intermediate 10tert-butyl 3-(5-cyanoindolin-l-yl)pyrrolidine-l-carboxylate[0109] To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaC BH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.
		tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate To a solution of <strong>[15861-23-1]indoline-5-carbonitrile</strong> (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-1-carboxylate (166 mg, 0.90 mmol) and HOAc (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

References: [1]Patent: WO2012/22265,2012,A1 .Location in patent: Page/Page column 34.
[2]Patent: WO2012/22045,2012,A1 .Location in patent: Page/Page column 29-30.
[3]Patent: US2013/210831,2013,A1 .Location in patent: Paragraph 0212.

17
[ 75-15-0 ]
[ 15861-23-1 ]
[ 74-88-4 ]
[ 1401726-66-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of NaH (2.5 g, 108 mmol) in DMF (100 mL) at 0 C. was added <strong>[15861-23-1]2,3-dihydro-1H-indole-5-carbonitrile</strong> (6.2 g, 43.0 mmol). After 15 min, CS2 (3.8 mL, 64.6 mmol) was added followed by MeI (4.0 mL, 64.6 mmol). The reaction mixture was stirred for 1 h at room temperature. The reaction mixture was then was poured onto ice. The resulting mixture was filtered. The remanence was washed with methylene chloride to give 5-cyano-2,3-dihydroindole-1-carbodithioic acid methyl ester as a off-white solid (7.5 g, 76%). The material was used without further purification.

References: [1]Patent: US2012/252853,2012,A1 .Location in patent: Page/Page column 22.

18
[ 15861-23-1 ]
[ 1401726-65-5 ]

References: [1]Patent: US2012/252853,2012,A1 .

19
[ 15861-23-1 ]
[ 1401726-67-7 ]

References: [1]Patent: US2012/252853,2012,A1 .

20
[ 15861-23-1 ]
[ 1401726-68-8 ]

References: [1]Patent: US2012/252853,2012,A1 .

21
[ 15861-23-1 ]
[ 1401726-69-9 ]

References: [1]Patent: US2012/252853,2012,A1 .

22
[ 15861-23-1 ]
1-(3,5-dihydroxyphenyl)indoline-5-carbonitrile [ No CAS ]

References: [1]Journal of Materials Chemistry A,2015,vol. 3,p. 17704 - 17712.

23
[ 15861-23-1 ]
4-((3-butyl-1,1-dimethyl-1H-benzo[e]indol-3-ium-2-yl)methylene)-2-(4-(5-cyanoindolin-1-yl)-2,6-dihydroxyphenyl)-3-oxocyclobut-1-enolate [ No CAS ]

References: [1]Journal of Materials Chemistry A,2015,vol. 3,p. 17704 - 17712.

24
[ 20469-65-2 ]
[ 15861-23-1 ]
1-(3,5-dimethoxyphenyl)indoline-5-carbonitrile [ No CAS ]

References: [1]Journal of Materials Chemistry A,2015,vol. 3,p. 17704 - 17712.

25
[ 15861-23-1 ]
[ 61394-92-1 ]