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[ CAS No. 868066-91-5 ]

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2D
Chemical Structure| 868066-91-5
Chemical Structure| 868066-91-5
Structure of 868066-91-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 868066-91-5 ]

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Related Doc. of [ 868066-91-5 ]

SDS

Product Details of [ 868066-91-5 ]

CAS No. :868066-91-5MDL No. :MFCD12755780
Formula :C9H8BrNOBoiling Point :356.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :226.07Pubchem ID :23158169
Synonyms :

Computed Properties of [ 868066-91-5 ]

TPSA : 20.3 H-Bond Acceptor Count : 1
XLogP3 : 1.6 H-Bond Donor Count : 0
SP3 : 0.22 Rotatable Bond Count : 0

Safety of [ 868066-91-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 868066-91-5 ]

  • Upstream synthesis route of [ 868066-91-5 ]
  • Downstream synthetic route of [ 868066-91-5 ]

[ 868066-91-5 ] Synthesis Path-Upstream   1~10

  • 1
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YieldReaction ConditionsOperation in experiment
71% at 50℃; Sealed tube [00530] Intermediate 51 b: 5-bromo-2-methyl-isoindolin-1 -one[00531] To a reaction tube containing methyl 4-bromo-2-(bromomethyl)benzoate (1 .2g, 3.gmmol) was added methylamine (2.OM in THF, lOmL, 2Ommol). The tube was sealed and the mixture was stirred and heated at 50 °C overnight. The mixture was then cooled to room temperature, filtered and the precipitate washed with THF. The filtrate was concentrated in vacuo and the residue waspurified by column chromatography using an eluent of 0-100percent EtOAc in heptane to give 5-bromo-2- methyl-isoindolin-1-one (623mg, 2.7Smmol, 71percent yield) as a white solid.1H NMR (CDCI3, 400MHz) O/ppm: 7.73-7.68 (1H, m), 7.64-7.56 (2H, m), 4.36 (2H, 5), 3.19 (3H, 5). MS Method 3: RT: 3.18 mi m/z226.0/228.0 [M+H]
68% With triethylamine In tetrahydrofuran at 100℃; for 12.00 h; Sealed tube Synthesis of 5-bromo-2-methylisoindolin-1-one (2)
A mixture of methyl 4-bromo-2-(bromomethyl)benzoate (1, 1 g, 3.26 mmol), 2 M methylamine in tetrahydrofuran (1.95 mL, 3.9 mmol) and triethylamine (0.9 mL, 6.52 mmol) was heated at 100° C. for 12 h in a sealed tube.
After completion of the reaction, the mixture was concentrated under reduced pressure.
The obtained residue was diluted with ethyl acetate and washed with water.
The organic was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure.
The residue was triturated with hexane to afford 5-bromo-2-methylisoindolin-1-one (2). Yield: 0.5 g, 68percent; MS (ESI) m/z 226, 228 [M+1]+.
0.112 g at 90℃; for 24.00 h; Step A: 5-bromo-2-methylisoindolin-l-one [0234] Methyl 4-bromo-2-(bromomethyl)benzoate (0.153 g, 0.497 mmol) was suspended in methanamine (2M solution in MeOH, 2.484 mL, 4.97 mmol) and the mixture was heated to reflux (90°C) for 24 hours. The reaction mixture was cooled, concentrated in vacuo, and dried under high vacuum to give the title compound (0.112 g). lU NMR (500 MHz, CDC13) δ ppm 3.19 (s, 3 H), 4.36 (s, 2 H), 7.57 - 7.62 (m, 2 H), 7.70 (d, J=8.30 Hz, 1 H); ESI-MS m/z [M+H]+ 226.3.
Reference: [1] Patent: WO2016/51193, 2016, A1. Location in patent: Paragraph 00527; 00530; 00531
[2] Patent: US10112955, 2018, B2. Location in patent: Page/Page column 29
[3] Patent: WO2013/148603, 2013, A1. Location in patent: Paragraph 0233-0234
[4] Patent: EP3406612, 2018, A1. Location in patent: Paragraph 0086; 0087
  • 2
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YieldReaction ConditionsOperation in experiment
80%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.50 h; Inert atmosphere
Stage #2: at 20℃; for 1.00 h; Inert atmosphere
General procedure: Bromoisoindolin-1-one (2.0 g, 9.43 mmol) was dissolved with warming in DMF (150 mL),then cooled to 0°C. NaH (415 mg, 10.4 mmol) was added and the mixture stirred under N2 at 0°C for 0.5 h. Methyl iodide (0.65 mL, 10.4 mmol) was added dropwise and the reaction allowed to warm to room temperature and stir for another I h. A small quantity of water was added to quench the reaction then the DMF removed under reduced pressure to give an oily yellow residue which was dissolved in EtOAc (150 mL). This solution waswashed with water (3x100 mL), brine (100 mL) and dried (Na2SO4)., Removal of the solvent under reduced pressure gave a solid which was purified by filtration through a plug of silica gel (10percent acetone/CH2C12 as eluant). The title compound was isolated as a very pale yellow crystalline solid (1.64 g, 80percent). ‘ H NMR [400 MHz, (CD3)2S0] ö 7.85 (dd, J= 1.5, 0.6 Hz, 1 H), 7.66 (dd, J= 8.0, 1.7 Hz, 1 H), 7.59 (d, J— 8.0 Hz, I H), 4.46 (s,2 H), 3.05 (s, 3 H). LRMS (APCI) calcd for C9H8BrNO 226, 228 (MH), found 226, 228.
61.9%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.50 h; Inert atmosphere
Stage #2: at 0℃; for 2.00 h;
5-Bromo-2-methylisoindolin-1-one
To a solution of 5-bromoisoindolin-1-one (2500 mg, 11.79 mmol) in DMF (20 mL) under nitrogen, at 0 °C, was added NaH (566 mg, 14.15 mmol) and the mixture was stirred for 30 min. After which, Mel (0.885 mL, 14.15 mmol) was added dropwise and the mixture was stirred at 0 °C for 2 h. The reaction was quenched with sat. aqueous NH4CI, and extracted with EtOAc (3 x 30 mL). The organic layer was washed with brine, dried and concentrated to afford 5-bromo-2-methylisoindolin-1-one (2500 mg, 7.30 mmol, 61.9 percent yield). LC-MS: m/z 226 (M+H)+1.02 min (ret. time).
Reference: [1] Patent: WO2014/28968, 2014, A1. Location in patent: Page/Page column 64
[2] Patent: WO2015/92713, 2015, A1. Location in patent: Page/Page column 572
  • 3
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YieldReaction ConditionsOperation in experiment
57.3%
Stage #1: at 0 - 20℃; for 0.50 h;
Stage #2: at 0 - 20℃; for 4.00 h;
A 150 mL sealed tube was charged with 4-bromo-2- (hydroxymethyl) -N-tnethylbenzamide (3.34 g, 13.7 mmol) and 1,3- dimethylimidazolidin-2-one (40.4 ml, 369 mmol). The solution was cooled to 00C and Isopropylmagnesium chloride (15.3 ml, 30.5 mmol) was added slowly. The tube was capped and the reaction mixture was stirred at room temperature for 30 minutes. This was recooled to 00C and N,N,N,N- tetramethylphosphorodiamidoyl chloride (2.64 ml, 17.8 mmol) was added in one portion; this mixture was stirred at room temperature for 4 hours. The tube was placed in a 150°C oil bath for 1 hour. The mixture was then diluted with EtOAc (100 mL) , then washed with IM aqueous HCl . The aqueous layer was extracted with ethyl acetate (3 x 100 mL) and then the combined organics were washed with water (100 mL) and brine (100 mL) , dried with MgSO4, filtered, then concentrated to give a yellow oil . This was purified by column chromatography, eluting with 1 - 4percent MeOH/DCM to give 5-bromo-2-methylisoindolin-l-one (1.774 g, 57.3percent yield) as a yellow solid.
Reference: [1] Patent: WO2008/8539, 2008, A2. Location in patent: Page/Page column 102
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Reference: [1] Synlett, 2006, # 5, p. 801 - 803
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Reference: [1] Patent: WO2010/128324, 2010, A1. Location in patent: Page/Page column 119
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Reference: [1] Patent: WO2014/28968, 2014, A1
[2] Patent: WO2015/92713, 2015, A1
[3] Patent: WO2016/51193, 2016, A1
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Reference: [1] Synlett, 2006, # 5, p. 801 - 803
  • 8
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Reference: [1] Synlett, 2006, # 5, p. 801 - 803
  • 9
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Reference: [1] Patent: WO2014/28968, 2014, A1
[2] Patent: WO2015/92713, 2015, A1
  • 10
  • [ 68837-59-2 ]
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Reference: [1] Patent: WO2014/28968, 2014, A1
[2] Patent: WO2015/92713, 2015, A1
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