387350-92-7|5-(Methylsulfonyl)indoline| Ambeed

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Quality Control of [ 387350-92-7 ] Purity: 95% SDS Specification

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Product Details of [ 387350-92-7 ]

CAS No. :	387350-92-7
Formula :	C₉H₁₁NO₂S
M.W :	197.25
SMILES Code :	CS(=O)(=O)C1=CC2=C(NCC2)C=C1
MDL No. :	MFCD01319203
InChI Key :	OFYOHQMIBTVTKY-UHFFFAOYSA-N
Pubchem ID :	2736136

Safety of [ 387350-92-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 387350-92-7 ]

* 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 [ 387350-92-7 ]

[ 387350-92-7 ] Synthesis Path-Downstream 1~35

1
[ 387350-92-7 ]
(S)-2-(3-((tert-butoxycarbonylamino)methyl)-4-(2,4-dichlorophenyl)-2-methyl-5-oxo-5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)-acetic acid [ No CAS ]
C₃₁H₃₂Cl₂N₄O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 20℃; for 1h;	A mixture of Example 50E (31.4 mg, 0.065 mmol), EDCI (49.8 mg, 0.26 mmol), HOAT (13.3 mg, 0.097 mmol) and <strong>[387350-92-7]5-(methylsulfonyl)indoline</strong> (16.7 mg, 0.084 mmol) was stirred at ambient temperature for 1 h and evaporated under reduced pressure. The residue was partitioned between EtOAc and H2O and the aqueous layer was extracted further with EtOAc. The combined organic layers were washed with brine, dried (NaSO4) and concentrated in vacuo. The residue was then dissolved in CH2Cl2 (1.0 mL) followed by addition of TFA (0.5 mL). The reaction mixture was allowed to stir at ambient temperature for 3 h and concentrated in vacuo. The crude product was purified by prep HPLC (Phenomenex Luna 5μ, 21.2×250 mm, 15 min gradient, 30 to 90% solvent B, 40 mL/min) to give Example 3, TFA salt (3.5 mg, 8% yield in 2 steps) as an off-white powder. 1H NMR (500 MHz, CD3OD) δ 2.77 (s, 3H), 2.99 (s, 3H), 3.25 (t, J=8.5 Hz, 2H), 3.88 and 4.12 (ABq, J=14.3 Hz, 2H), 4.18 (t, J=8.5 Hz, 2H), 4.44 and 4.55 (ABq, J=16.0 Hz, 2H), 4.58 (s, 2H), 7.26 (d, J=8.3 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.60 (s, 1H), 7.66 (d, J=8.3 Hz, 1H), 7.71 (s, 1H), 8.13 (d, J=8.8 Hz, 1H). HRMS: Calculated for C26H25Cl2N4O4S: 559.0974. Found: 559.0985 [M+H]+.

References: [1]Patent: US2006/264457,2006,A1 .Location in patent: Page/Page column 69.

2
[ 387350-92-7 ]
[ 920036-24-4 ]
3-chloro-5-(2-chloro-5-{2-[5-(methylsulfonyl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethoxy}phenoxy)benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2959 - 2966.

3
[ 387350-92-7 ]
[ 152879-73-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With manganese(IV) oxide; In dichloromethane; at 20℃;	Example 112; 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-methanesulfonyl-indol-l-yl)-amide; Step 1 : A solution of 5-methanesulfonyl-indoline (4.11 mmol) and MnO2 (20.55 mmol) in DCM (20 mL) is stirred at rt overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo to afford 5 -methanesulfonyl- 1 H-indole (782 mg, 100%) as a solid. MS: 196 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.09 (s, 3H), 6.71 (s, H), 7.39 (s, H), 7.53 (d, H), 7.74 (m, H), 8.30 (s, H), 8.66 (br, N-H).
71%	With manganese(IV) oxide; In chloroform; at 20℃; for 9h;	(a) Step 1 A solution of <strong>[387350-92-7]5-(methylsulfonyl)indoline</strong> (0.213 g, 1.08 mmol) in chloroform (4 mL) was added with manganese dioxide (0.939 g, 10.8 mmol), and the mixture was stirred at room temperature for 9 hours. The reaction mixture was filtered through Celite, and the resulting filtrate was concentrated to obtain 5-(methylsulfonyl)-1H-indole (0.151 g, 71%). 1H NMR (300 MHz, DMSO-d6) δ 3.08 (s, 3H), 6.71 (t, J = 2.2 Hz, 1H), 7.38 (t, J = 2.9 Hz, 1H), 7.53 (d, J = 8.8 Hz, 1H), 7.72-7.75 (m, 1H), 8.30 (br s, 1H), 8.57 (br s, 1H).

References: [1]Patent: WO2008/121670,2008,A1 .Location in patent: Page/Page column 129.
[2]Patent: EP2565192,2013,A1 .Location in patent: Paragraph 0493.

4
[ 791852-35-2 ]
[ 387350-92-7 ]
[ 1196484-67-9 ]

Yield	Reaction Conditions	Operation in experiment
21%	With caesium carbonate; In N,N-dimethyl-formamide; at 70℃;	Example 104-[4-(5-Methanesulfonyl-2,3-dihydro-indol-1-yl)-pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester; 5-(Methylsulfonyl)-indoline (Matrix Scientific, Columbia, S.C., USA; 30 mg, 0.15 mmol) and triethylamine (70 μL, 0.5 mmol) were added to a solution of 4-(4-chloro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (Intermediate 19; 45 mg, 0.133 mmol) in tetrahydrofuran (1 mL). The mixture was heated to reflux. No reaction had occurred after 2 h. The volatiles were evaporated. Dimethylformamide (1 mL) and cesium carbonate (250 mg, 0.77 mmol) were added. The mixture was heated at 70 C. overnight, then poured into saturated aqueous sodium bicarbonate, and extracted three times with ethyl acetate. The combined organic extracts were washed twice with water and once with brine, dried (magnesium sulfate), filtered, evaporated, and purified by column chromatography eluting with ethyl acetate to give 4-[4-(5-methanesulfonyl-2,3-dihydro-indol-1-yl)pyrazolo[3,4-d]pyrimidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (14 mg, 21%) as an off-white solid.

References: [1]Patent: US2009/286812,2009,A1 .Location in patent: Page/Page column 35.

5
[ 2831-66-5 ]
[ 387350-92-7 ]
[ 1259510-74-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With 2,6-dimethylpyridine; In toluene; at 0 - 20℃;	To a stirred solution of compound 1 (190 mg, 0.991 mmol) and 2,4-dichloro-1,3,5-triazine (165 mg, 1.10 mmol) in toluene (10 mL) was added 2,6-lutidine (0.150 mL, 1.29 mmol) at 0 C. After being stirred at room temperature overnight, the mixture was quenched with water and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt = 95/5 to 65/35) to give the title compound as colorless solid (135 mg, 39%). MS (ESI) m/z 311 [M+H]+. 1H NMR (300 MHz, CDCl3) δ 3.06 (3H, s,, 3.32 (2H, t, J = 8.7 Hz), 4.38 (2H, t, J = 8.3 Hz), 7.81 (1H, s), 7.88 (1H, t, J = 6.4 Hz), 8.56 (1H, dd, J = 14.7, 8.7 Hz) 8.66 (1H, d, J = 5.7 Hz).
	With tol-BINAP; caesium carbonate;palladium diacetate; In 1,4-dioxane; at 100℃; for 4h;	5-Methanesulfonyl-2,3-dihydro-lH-indole (79 mg, 0.4 mmol) was dissolved in dioxane (2 mL). 2,4-Dichloro-[l,3,5]triazine (60 mg, 1 eq), palladium acetate (11 mg, 5% molar), (+/-)binap (15 mg, 8% molar) and cesium carbonate (131 mg, 1 eq) were added and the reaction mixture was heated at 100 0C for 4h. The mixture was cooled to room temperature and water was added. The mixture was filtered through celite and washed three times with dioxane. The collected filtrate was evaporated to dryness to give Ha (104 mg) which was used for the next step without further purification

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1649 - 1666.
[2]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 44.

6
[ 1193-21-1 ]
[ 387350-92-7 ]
[ 1145658-37-2 ]

Yield	Reaction Conditions	Operation in experiment
71%		Reference Example 17 1-(6-chloropyrimidin-4-yl)-<strong>[387350-92-7]5-(methylsulfonyl)-2,3-dihydro-1H-indole</strong>; A mixture of 4,6-dichloropyrimidine (4.1 g, 27.5 mmol), <strong>[387350-92-7]5-(methylsulfonyl)-2,3-dihydro-1H-indole</strong> (5.0 g, 25.0 mmol), and ethanol (160 mL) was heated under reflux for 4 hr. The reaction mixture was concentrated, aqueous sodium hydrogen carbonate solution was added thereto, and the resulting solid was washed with water and dried under reduced pressure to give the title compound (5.5 g, yield 71%) as colorless crystals. 1H-NMR (300 MHz, DMSO-d6)δ:3.17 (s, 3 H), 3.24 - 3.37 (m, 2 H), 4.16 (t, J=8.7 Hz, 2 H), 7.09 (s, 1 H), 7.73 - 7.85 (m, 2 H), 8.57 (d, J=9.4 Hz, 1 H), 8.68 (s, 1 H).
71%		A mixture of 4,6-dichloropyrimidine (4.10 g, 27.5 mmol), compound 1 (5.00 g, 25.0 mmol), and EtOH (160 mL) was refluxed for 4 h. After the mixture was concentrated under reduced pressure, to the residue was added aqueous NaHCO3 solution. The precipitated solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound as a colorless solid (5.50 g, 71%). 1H NMR (300 MHz, DMSO-d6) δ 3.17 (3H, s), 3.24-3.37 (2H, m), 4.16 (2H, t, J = 8.7 Hz), 7.09 (1H, s), 7.73-7.85 (2H, m), 8.57 (1H, d, J = 9.4 Hz), 8.68 (1H, s).
71%	In ethanol; for 4h;Reflux;	A mixture of 4,6-dichloropyrimidine (4.10g, 27.5mmol), <strong>[387350-92-7]5-(methylsulfonyl)-2,3-dihydro-1H-indole</strong> (5.00g, 25.0mmol), and EtOH (160mL) was refluxed for 4h. After the mixture was concentrated under reduced pressure, saturated aqueous NaHCO3 solution was added to the residue. The precipitated solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound as a colorless solid (5.50g, 71%). MS (ESI/APCI) m/z 310 [M+H]+. 1H NMR (300MHz, DMSO-d6) δ 3.17 (3H, s), 3.24-3.37 (2H, m), 4.16 (2H, t, J=8.7Hz), 7.09 (1H, s), 7.73-7.85 (2H, m), 8.57 (1H, d, J=9.4Hz), 8.68 (1H, s).

41%

To a suspension of sodium hydride (0.24 g, 1.5 eq) in 10 rnL of DMF at 0 0C, was added 5-methanesulfonyl-2,3-dihydro-lH-indole (0.8 g , 4.05 mmol). The mixture was stirred at 0 0C for 10 minutes, then 4,6-pyrimidine dichloride (0.8 g, 1 eq) was added. The resulting mixture was stirred at room temperature for 4h. The reaction mixture was then quenched with brine (100 mL) and extracted with ethyl acetate (100 mL then 3 x 50 mL). The combined extracts were washed with brine, dried over magnesium sulfate and filtered. The solvent was removed under vacuum and the crude product was purified by 3 consecutive column chromatography (elution with 25-100% ethyl acetate and 0.1% TEA in hexanes) to give 0.51 g of 6a (41% yield).

References: [1]Patent: EP2399914,2011,A1 .Location in patent: Page/Page column 94.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1649 - 1666.
[3]Bioorganic and Medicinal Chemistry,2021,vol. 41.
[4]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 38.
[5]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 373 - 379.

7
[ 442199-19-1 ]
[ 387350-92-7 ]
[ 1145657-02-8 ]

Yield	Reaction Conditions	Operation in experiment
40%		To a suspension of sodium hydride (0.25 g, 2 eq) in 10 mL of DMF, was added 5- methanesulfonyl-2,3-dihydro-lH-indole (0.63 g , 1 eq). The mixture was stirred at room temperature for 10 minutes then 3a (1 g, 3.19 mmol) was added. The resulting mixture was heated up to 80 0C for 18h. The reaction mixture was then allowed to cool down to room temperature and brine (200 mL) was added. The solution was extracted with DCM twice (200 mL then 50 mL). The combined extracts were washed with brine (2 x 50 mL), dried over magnesium sulfate and filtered. The solvent was removed under vacuum to give an oil which was purified by column chromatography (elution with 10-100% ethyl acetate and 0.1% TEA in hexanes) to give 0.61 g of 4a (40% yield), LCMS 475.2 (MH+).

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 35; 36.

8
[ 871681-78-6 ]
[ 387350-92-7 ]
[ 1259510-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; oil; at 90℃; for 1h;	Each product (10a and 10b) (30 mg, 0.1 mmol) was then separately taken up with DMF and 5-methanesulfonyl-2,3-dihydro-lH-indole was added (20 mg, 1 eq). To this mixture, was added sodium hydride (60% in oil, 6 mg, 1.5 eq) and the reaction mixture was heated at 90 0C for Ih. At room temperature, the reaction mixture was then quenched with water and partitioned between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The crude products (10-1 and 10-2) were purified by preparative HPLC, LCMS 460.1 (MH+). tR = 4.72 (Method 2), EC50: 588 nM for 10-1 and LCMS 460.2 (MH+). tR = 5.21 (Method 6) for 10-2

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 43.

9
[ 897732-25-1 ]
[ 387350-92-7 ]
[ 1145657-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 90℃; for 4h;	A mixture of 8a (49 mg, 0.15 mmol), cesium carbonate (0.11 g, 2 eq), 5- Methanesulfonyl-2,3-dihydro-lH-indole (35 mg, 1.2 eq), tris(dibenzylideneacetone)- dipalladium (31 mg, 0.1 eq), tri-t-butylphosphonium tetrafluoroborate (37 mg, 0.8 eq) and dioxane (1.5 mL) was heated at 90 0C for 4h. The mixture cooled to room temperature, dioxane was added and the mixture was filtered and washed with DCM. The filtrate was concentrated under a stream of nitrogen and the residue was taken up in 1 mL of THF and was purified by preparative HPLC to afford 8-1; LCMS 491.2 (MH+), tR = 5.35 (Method 6). EC50: 201 nM. .

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 41.

10
[ 387350-92-7 ]
[ 1259510-83-2 ]
[ 1259510-82-1 ]
[ 1259510-50-3 ]
[ 1259510-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tol-BINAP; caesium carbonate;palladium diacetate; In 1,4-dioxane; at 100℃; for 4h;	0.19 g (0.6 mmol) of the mixture of 12a and 12b was dissolved in dioxane (3 mL) along with 5-methanesulfonyl-2,3-dihydro-lH-indole (0.12 g, 1 eq), cesium carbonate (0.19 g, 1 eq), palladium acetate (16 mg, 3% molar) and (+/-)-binap (22 mg, 6% molar). The mixture was heated at 100 0C for 4h, cooled to room temperature, filtered through celite and washed with DCM. The organic layer was collected and evaporated to dryness. The residue was dissolved in methanol and DCM and purified by preparative HPLC to give 12-1 and 12-2; LCMS 475.2 (MH+), tR = 4.58 (Method 6) for 12-1 and LCMS 475.2 (MH+), tR = 5.55 (Method 6) for 12-2.

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 45.

11
[ 387350-92-7 ]
[ 1259510-75-2 ]
[ 1259510-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 90℃; for 4h;	14a (100 mg) was dissolved in DMF with 5-methanesulfonyl-2,3-dihydro-lH- indole (0.3 mmol) and NaH (0.3 mmol). The mixture was heated at 90 0C for 4h. After cooling to room temperature, the mixture was diluted with ethyl acetate and water. The organic layer was washed with a saturated NaHCOs solution, isolated, evaporated and purified by preparative HPLC to give 14-1, LCMS 475.1 (MH+).

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 47.

12
[ 387350-92-7 ]
[ 939986-76-2 ]
[ 1240301-00-1 ]

Yield	Reaction Conditions	Operation in experiment
62%		To a solution of NaH (0.62 g, 15.5 mmol, 60% NaH) in 40 mL of DMF, 5- methanesulfonyl-2,3-dihydro-lH-indole (1.9 g, 9.63 mmol) was added and the mixture was stirred at room temperature for 30 minutes. 17a (3.09 g, 9.88 mmol) was added in DMF and the mixture was heated at 85 0C for 17h. After cooling to room temperature, brine was added (200 mL) and the mixture was extracted with DCM (200 mL then 3 x 500 mL). The combined extracts were washed with brine (3 x 100 mL), dried, filtered and evaporated. The residue was purified by flash chromatography (eluent : 25 to 100% EtOAc in hexane with 0.1% triethylamine) to afford 2.83 g (62 %) of 17b

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 49.

13
[ 387350-92-7 ]
[ 871681-77-5 ]
[ 1259510-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; oil; at 90℃; for 1h;	Each product (10a and 10b) (30 mg, 0.1 mmol) was then separately taken up with DMF and 5-methanesulfonyl-2,3-dihydro-lH-indole was added (20 mg, 1 eq). To this mixture, was added sodium hydride (60% in oil, 6 mg, 1.5 eq) and the reaction mixture was heated at 90 0C for Ih. At room temperature, the reaction mixture was then quenched with water and partitioned between ethyl acetate and water. The organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The crude products (10-1 and 10-2) were purified by preparative HPLC, LCMS 460.1 (MH+). tR = 4.72 (Method 2), EC50: 588 nM for 10-1 and LCMS 460.2 (MH+). tR = 5.21 (Method 6) for 10-2

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 43.

14
[ 387350-92-7 ]
[ 871681-77-5 ]
[ 1259510-78-5 ]
[ 1259510-79-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 10a (0.15 g, 0.5 mmol) in 2 rnL of acetonitrile, was added bromine(0.1 mL, 1.95 mmol). The mixture was stirred at room temperature for 6h then evaporated. The residue was added to a pre-stirred suspension of NaH (60% in oil, 9 mg, 0.22 mmol) and 5-methanesulfonyl-2,3-dihydro-lH-indole (43 mg, 0.22 mmol) in 1 mL of DMF. The mixture was stirred at 90 0C for 12h, quenched with water, extracted with ethyl acetate and evaporated. The residue was purified by silica gel chromatography (eluent : 20% ethyl acetate in hexane) to afford 24a and 24b (80 mg of the less polar product and 55 mg of the more polar product).

References: [1]Patent: WO2010/149685,2010,A1 .Location in patent: Page/Page column 57.

15
[ 387350-92-7 ]
[ 1259510-48-9 ]