316181-82-5|3-Acetyl-6-bromoindole| Ambeed

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Quality Control of [ 316181-82-5 ] Purity: 95% SDS Specification

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Product Details of [ 316181-82-5 ]

CAS No. :	316181-82-5
Formula :	C₁₀H₈BrNO
M.W :	238.08
SMILES Code :	BrC1=CC2=C(C=C1)C(C(C)=O)=CN2
MDL No. :	MFCD09834653
InChI Key :	JKNOMMZAFCVSGO-UHFFFAOYSA-N
Pubchem ID :	23245462

Safety of [ 316181-82-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 316181-82-5 ]

* 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 [ 316181-82-5 ]

[ 316181-82-5 ] Synthesis Path-Downstream 1~35

1
[ 52415-29-9 ]
[ 75-36-5 ]
[ 316181-82-5 ]

Yield	Reaction Conditions	Operation in experiment
68%		To a solution of 6-bromo-lH-indole (202a) (5 g, 25.5 mmol) in toluene (80 mL) at 0 C under inert atmosphere was added acetyl chloride (2.72 mL, 38.3 mmol), stirred for 10 mins followed by dropwise addition of Tin(IV) chloride (4.49 mL, 38.3 mmol) in toluene (20 mL). The reaction mixture was stirred at 0 C for 3h in ice-water bath and the pink fine suspension was poured into a bi-phasic layer of aqueous saturated NaHCCb (600 mL) and EtOAc (400 mL). The mixture was stirred vigorously for 15 min and filtered over Celite pad to remove inorganic impurities. The organic layer was separated washed with brine, dried, filtered and concentrated in vacuum to afford l-(6-bromo-lH-indol-3-yl)ethanone (202b) (4.15 g, 17.43 mmol, 68% yield) as a white solid; 1H MR (300 MHz, OMSO-de) δ 12.04 (s, 1H), 8.34 (d, J = 1.6 Hz, 1H), 8.10 (dd, J = 8.5, 0.6 Hz, 1H), 7.65 (dd, J = 1.8, 0.6 Hz, 1H), 7.31 (dd, J = 8.5, 1.8 Hz, 1H), 2.44 (s, 3H); MS (ES+): 238.2, 240.2 (M+2); MS (ES-): 236.1, 238.1 (M-2).
62%		At room temperature, dissolve 6-bromoindole (7) (15.0g, 76.5mmol) in anhydrous toluene (150mL), cool to 0C, add acetyl chloride (10.9mL, 153.0mmol), Stir at 0 C for 15 min. Then add tin tetrachloride (17.9ml, 153.0 mmol) in toluene (75mL), stir the reaction at 0C for 2h. TLC monitoring, after the reaction is complete, add 8% sodium bicarbonate solution (75mL) dropwise, then add ethyl acetate (150 mL), stirring at room temperature for 10 min. The organic layer was separated, the aqueous layer was extracted with ethyl acetate (150 mL*2), the organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered with suction, concentrated under reduced pressure and evaporated to remove the solvent to obtain a brown solid. Recrystallized with acetone to obtain 11.3g of gray solid with a yield of 62%.
11%		To a solution of 46-S1 (5 g, 25.5 mmol) in dry DCM (50 mL) was added SnCl4 (5 mL) under an atmosphere of nitrogen at 0 C. The mixture was stirred at this temperature for 30 minutes and acetyl chloride (3.0 g, 38.3 mmol) was added dropwise to the reaction mixture, followed by nitromethane (30 mL). The reaction mixture was stirred at room temperature for 4 hours. The mixture was quenched with ice water and extracted with DCM twice. The combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness. The remaining residue was purified by column chromatography on silica gel (eluted with DCM/MeOH = 100:1) to afford 46-S2 (669 mg, 11% yield) as a yellow solid. LC/MS (ESI) m/z: 238/240 (M+H)+.

	With tin(IV) chloride; In toluene;Inert atmosphere;	[0505] 1-(6-Bromo-1H-indol-3-yl)ethanone 51 was prepared from 6-bromoindole 50 according to the procedure of MacKay et al. (MacKay, J. A.; Bishop, R.; Rawal, V. H. Org. Lett. 2005, 7, 3421-3424.)
		General procedure: To a CH2Cl2 solution of indole A was added Et2AlCl (1.5 equiv, 2M in hexane) dropwise at 0 C. After stirred for 30 min, the substituted acid chlorides were added dropwise to this solution at 0 C. The resulting mixture was allowed to stir at same temperature for 2-4 hours. After completion of the reaction it was quenched with aqueous buffer (Ph = 7) and extracted by CH2Cl2. The organic layer was dried over anhydrous Na2SO4, concentrated under pressure and then purified by column chromatography on silica gel to provide the indole B. Indole B was suspended in N, N-dimethylformamaide (DMF) and NaH (1.5 equiv) was added under ice cooled conditions. Then DMF solution of TsCl (1.2 equiv) was added dropwise at 0 C. After stirred at room temperature overnight, the mixture was quenched with water and then extracted with CH2Cl2 three times. The organic layer was dried over anhydrous Na2SO4, concentrated under pressure and then purified by column chromatography on silica gel to provide the N-Ts indoles C. Under argon, a flask was charged with the N-Ts indoles C and anhydrous THF. Under the ice cooled conditions, Grignard reagents (1M in THF, 1.5 equiv) were added dropwise. Then, the reaction mixture was stirred at 50 C overnight. After completion of the reaction it was quenched with a saturated solution of NH4Cl and extracted with CH2Cl2. Combined organic layers were dried over Na2SO4, the solvent was evaporated and the residue was purified by a silica gel chromatography column to afford the 3-indolymethanols D (1a-1p).

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4474 - 4489.
[2]Patent: WO2017/136395,2017,A1 .Location in patent: Page/Page column 267; 268.
[3]Journal of Natural Products,2015,vol. 78,p. 355 - 362.
[4]Patent: CN111777613,2020,A .Location in patent: Paragraph 0198-0201.
[5]Tetrahedron,2001,vol. 57,p. 2355 - 2363.
[6]Patent: WO2018/160891,2018,A1 .Location in patent: Page/Page column 562-563.
[7]Chemical Communications,2017,vol. 53,p. 3945 - 3948.
[8]Patent: WO2017/35357,2017,A1 .Location in patent: Paragraph 0461; 0505.
[9]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 702 - 707.
[10]Organic Letters,2019,vol. 21,p. 9898 - 9903.
[11]Organic Letters,2020.
[12]ChemMedChem,2020,vol. 15,p. 1672 - 1679.
[13]Chinese Chemical Letters,2021,vol. 32,p. 1915 - 1919.
[14]Chemistry - A European Journal,2021,vol. 27,p. 13123 - 13127.

2
[ 98-59-9 ]
[ 316181-82-5 ]
[ 224434-85-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a CH2Cl2 solution of indole A was added Et2AlCl (1.5 equiv, 2M in hexane) dropwise at 0 C. After stirred for 30 min, the substituted acid chlorides were added dropwise to this solution at 0 C. The resulting mixture was allowed to stir at same temperature for 2-4 hours. After completion of the reaction it was quenched with aqueous buffer (Ph = 7) and extracted by CH2Cl2. The organic layer was dried over anhydrous Na2SO4, concentrated under pressure and then purified by column chromatography on silica gel to provide the indole B. Indole B was suspended in N, N-dimethylformamaide (DMF) and NaH (1.5 equiv) was added under ice cooled conditions. Then DMF solution of TsCl (1.2 equiv) was added dropwise at 0 C. After stirred at room temperature overnight, the mixture was quenched with water and then extracted with CH2Cl2 three times. The organic layer was dried over anhydrous Na2SO4, concentrated under pressure and then purified by column chromatography on silica gel to provide the N-Ts indoles C. Under argon, a flask was charged with the N-Ts indoles C and anhydrous THF. Under the ice cooled conditions, Grignard reagents (1M in THF, 1.5 equiv) were added dropwise. Then, the reaction mixture was stirred at 50 C overnight. After completion of the reaction it was quenched with a saturated solution of NH4Cl and extracted with CH2Cl2. Combined organic layers were dried over Na2SO4, the solvent was evaporated and the residue was purified by a silica gel chromatography column to afford the 3-indolymethanols D (1a-1p).

References: [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4474 - 4489.
[2]Tetrahedron,2001,vol. 57,p. 2355 - 2363.
[3]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 702 - 707.
[4]ChemMedChem,2020,vol. 15,p. 1672 - 1679.
[5]Chinese Chemical Letters,2021,vol. 32,p. 1915 - 1919.

3
[ 316181-82-5 ]
Meridianin D [ No CAS ]

References: [1]Tetrahedron,2001,vol. 57,p. 2355 - 2363.
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 4474 - 4489.

4
[ 316181-82-5 ]
[ 341998-58-1 ]

References: [1]Tetrahedron,2001,vol. 57,p. 2355 - 2363.
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 702 - 707.

5
[ 316181-82-5 ]
[ 290333-09-4 ]