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[ CAS No. 14548-39-1 ]

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Chemical Structure| 14548-39-1
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CAS No. :14548-39-1 MDL No. :MFCD02179286
Formula : C9H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :211.06 g/mol Pubchem ID :139778
Synonyms :

Safety of [ 14548-39-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 14548-39-1 ]

  • Upstream synthesis route of [ 14548-39-1 ]
  • Downstream synthetic route of [ 14548-39-1 ]

[ 14548-39-1 ] Synthesis Path-Upstream   1~15

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YieldReaction ConditionsOperation in experiment
42% With sodium azide; methanesulfonic acid In chloroform for 3 h; Reflux The compound 6-bromo-2,3-dihydro-1H-inden-1-one (2.0 g, 9.5 mmol) was dissolved in chloroform (30 mL)Methanesulfonic acid (6 mL) was then added dropwise to the reaction system,Finally, sodium azide (1.90 g, 9.5 mmol) was added portionwise to the reaction system,Reflux for three hours.After completion of the reaction, the mixture was cooled to room temperature, and then the reaction solution was poured into ice water. The mixture was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were dried over anhydrous sodium sulfate, filtered and dried. The crude product was purified by column chromatography (Petroleum ether / ethyl acetate: 2/1) to give 7-bromo-3,4-dihydroquinolin-2 (1H) -one(0.90 g) in 42percent yield.
Reference: [1] Patent: CN106349241, 2017, A, . Location in patent: Paragraph 0538; 0539; 0540; 0541; 0542
[2] Patent: WO2010/38901, 2010, A1, . Location in patent: Page/Page column 44
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667
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  • [ 58794-09-5 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5312 - 5315
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  • [ 83-33-0 ]
  • [ 15115-60-3 ]
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Reference: [1] Synthetic Communications, 1994, vol. 24, # 19, p. 2777 - 2788
[2] Patent: US5753655, 1998, A,
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  • [ 34598-49-7 ]
  • [ 103515-98-6 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 11, p. 2107 - 2114
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Reference: [1] European Journal of Organic Chemistry, 2001, # 11, p. 2107 - 2114
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Reference: [1] European Journal of Organic Chemistry, 2001, # 11, p. 2107 - 2114
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  • [ 34598-49-7 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 11, p. 2107 - 2114
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  • [ 67159-85-7 ]
Reference: [1] Patent: US2012/225857, 2012, A1,
  • 9
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  • [ 75476-86-7 ]
YieldReaction ConditionsOperation in experiment
100% With sodium tetrahydroborate In ethanol at 10 - 20℃; for 3 h; 168.8g compd. 6 and 650 ml of ethanol is added during the reaction of the bottle. Next, the water temperature is lower than 10 °C, NaBH445g of small amounts of added. Next, raised in temperature to room temperature, the reaction solution is a 3-hour continuous agitation. After the reaction is completed, ethanol is removed, then the hydrolysis of 10percent HCl 450 ml is added is in order. The mixture is extracted by dichlomethane, thereafter is washed with water, dried and then, the solvent is removed, 170g compd. 7 in which yield 100percent (corallite solid). The reaction of the pathway of the following relationships.
99% With sodium borohydrid In methanol Example 10 Part A,
6-Bromo-2,3-dihydro-1H-inden-1-ol
To a solution of 6-bromo-1-indanone (prepared as described by Cornelius, Lyndon A. M. and Combs, Donald W. Synth. Commun. (1994), 24(19), 2777-88) (1.4 g, 6.57 mmol) in 20 mL of methanol was added sodium borohydride (0.087 g, 2.3 mmol) over a period of five minutes at room temperature.
The reaction mixture was stirred for two hours at room temperature, concentrated under pressure and partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL).
The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound as a solid (1.4 g, 99percent).
1H NMR (CDCl3): δ 7.45 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 5.2 (t, 1H), 2.9 (m, 1H), 2.7 (m, 1H), 2.4 (m, 1H), 1.9 (m, 2H).
99% at 20℃; for 2 h; Inert atmosphere To a solution of 6-bromo-2,3-dihydro-1 H-inden-1 -one (5 g, 23.69 mmol) in methanol (50 mL) was added sodium borohydride (0.896 g, 23.69 mmol) under N2 protection. The reaction mixture was stirred for 2 h at ambient temperature. Then the solvent was removed by reduced pressure. The residue was dissolved inlOO mL of ethyl acetate and 20 mL of 1 N HCI. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 30 mL). Thecombined organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound 6-bromo-2,3-dihydro-1 H-inden-1 -ol (5.0 g, 23.47 mmol, 99percent). LC-MS m/z 195.0 (M-OH), 1.46 mm (ret. time).
99% at 20℃; for 2 h; Inert atmosphere To a solution of 6-bromo-2,3-dihydro-1H-inden-1-one (5 g, 23.69 mmol) in methanol (50 mL) was added sodium borohydride (0.896 g, 23.69 mmol) under N2 protection. The reaction mixture was stirred for 2 h at ambient temperature. Then the solvent was removed by reduced pressure. The residue was dissolved in100 mL of ethyl acetate and 20 mL of 1 N HCl. The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried over anhydrous Na2SO4 and concentrated to afford the title compound 6-bromo-2,3-dihydro-1H-inden-1-ol (5.0 g, 23.47 mmol, 99percent). LC-MS m/z 195.0 (M-OH)+, 1.46 min (ret. time).
97% at 20℃; for 2 h; Inert atmosphere To a solution of 6-bromo-2,3-dihydro-1H-inden-1-one (5 g, 23.69 mmol) in methanol (100 mL) was added sodium borohydride (0.986 g, 26.1 mmol) under N2. The reaction mixturewas stirred at ambient temperature for 2 hrs. The solvent was removed by reducedpressure. The residue was re-dissolved in 100 mL of ethyl acetate and 20 mL of iN HCI.The organic layer was separated and the aqueous layer was extracted with ethyl acetate(3x). The combined organic layer was washed with brine and dried over anhydrous Na2SO4.After filtration and concentration, the title compound 6-bromo-2,3-dihydro-1 H-inden-1 -ol (4.9g, 23.0 mmol, 97percent) was obtained and was carried over to next step without furtherpurification. LC-MS mlz 197.0 (M+H-18), 1.80 mm (ret. time)
96% for 0.5 h; Inert atmosphere Under N2 atmosphere, 6-bromo-1-indanone (1 mmol) was dissolved in MeOH (2.25 mL) and NaBH4 (1 mmol) was added in 3 portions, every 10 min. After 30 min, the solvent was evaporated and crude was dissolved in EtOAc (1 mL) and H2O (3 mL). The aqueous layer was extracted with EtOAc and the combined organic extracts were dried and concentrated to dryness to give pure alcohol in 96percent yield. 1H-NMR (400MHz, CDCl3) δ ppm: 7.3-7.2 (m, 2H), 7.14 (dd, , J=8 and 2 Hz, 1H), 5.26 (t, J=6 Hz, 1H,), 3.09-3.01 (m, 1H), 2.87-2.80 (m, 1H), 2.62-2.54 (m, 1H), 2.03-1.96 (m, 1H).
96% for 0.5 h; Inert atmosphere Under N2 atmosphere, 6-bromo-1 -indanone (1 mmol) was dissolved in MeOH (2.25 mL) and NaBH4 (1 mmol) was added in 3 portions, every 10 min. After 30 min, the solvent was evaporated and crude was dissolved in EtOAc (1 mL) and H20 (3 mL). The aqueous layer was extracted with EtOAc and the combined organic extracts were dried and concentrated to dryness to give pure alcohol in 96percent yield.1 H-NMR (400MHz, CDCI3) δ Dppm: 7.3-7.2 (m, 2H), 7.14 (dd, , J=8 and 2 Hz, 1 H), 5.26 (t, J=6 Hz, 1 H,), 3.09-3.01 (m, 1 H), 2.87-2.80 (m, 1 H), 2.62-2.54 (m, 1 H), 2.03- 1 .96 (m, 1 H).
95% With sodium tetrahydroborate In methanol at 20℃; for 2 h; To a solution of 6-bromoindan-1-one (Aldrich, cat No.597147: 250 mg, 1.2 mmol) in methanol (3 mL) was added sodium tetrahydroborate (49 mg, 1.3 mmol) in 2 portions.
The reaction mixture was stirred at room temperature for 2 h leading to complete conversion.
The solvent was removed and the residue was partitioned between water and EtOAc.
The EtOAc layer was washed with brine, dried over sodium sulfate, and the solvent was removed to obtain 6-bromoindan-1-ol (racemic, 240 mg, 95percent) which was used in the next step without further purification. LC-MS calculated for C9H8Br (M+H-H2O)+: m/z=195.0. found 195.0.

Reference: [1] Patent: JP2016/29040, 2016, A, . Location in patent: Paragraph 0058
[2] Patent: US2002/40022, 2002, A1,
[3] Patent: WO2016/203401, 2016, A1, . Location in patent: Page/Page column 58; 59; 60; 199
[4] Patent: WO2018/104766, 2018, A1, . Location in patent: Page/Page column 58-60; 200-201
[5] Patent: WO2018/109648, 2018, A1, . Location in patent: Page/Page column 83
[6] Patent: EP2308849, 2011, A1, . Location in patent: Page/Page column 13; 14
[7] Patent: WO2011/42343, 2011, A1, . Location in patent: Page/Page column 24
[8] Patent: US2016/9720, 2016, A1, . Location in patent: Paragraph 0495
[9] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
[10] Organic and Biomolecular Chemistry, 2003, vol. 1, # 8, p. 1298 - 1307
[11] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5312 - 5315
[12] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 12, p. 1657 - 1662
[13] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 3, p. 547 - 551
[14] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 5, p. 1333 - 1336
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Reference: [1] Patent: US5180741, 1993, A,
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  • [ 75476-78-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 8, p. 1298 - 1307
[2] Journal of Organic Chemistry, 1984, vol. 49, # 22, p. 4226 - 4237
[3] Journal of Organic Chemistry, 1980, vol. 45, # 26, p. 5312 - 5315
[4] Tetrahedron, 2010, vol. 66, # 44, p. 8557 - 8561
[5] Patent: JP2016/29040, 2016, A,
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  • [ 114744-51-3 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 662 - 667
  • 13
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  • [ 174349-93-0 ]
Reference: [1] Patent: JP2016/29040, 2016, A,
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  • [ 193819-51-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 16, p. 4371 - 4375
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YieldReaction ConditionsOperation in experiment
61% With sodium azide; methanesulfonic acid In dichloromethane at 0 - 20℃; Intermediate 23-1Preparation of 7-bromo-3,4-dihydroisoquinolin-1(2H)-one Sodium azide (0.431 g, 6.63 mmol) was added slowly to a mixture of 6-bromo-2,3-dihydro-1H-inden-1-one (1 g, 4.74 mmol) and methanesulfonic acid (15 mL, 231 mmol) in DCM (30 mL) at 0° C. The mixture was stirred at rt for 15 hrs, then was carefully quenched with 1 M aqueous sodium hydroxide (50 mL). The aqueous layer was extracted with DCM (3.x.50 mL), and the combined organic layers were washed with water (20 mL) and brine (20 mL), dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 hexane-EtOAc to EtOAc) to give 7-bromo-3,4-dihydroisoquinolin-1(2H)-one as white solid (650 mg, 61percent). 1H NMR (400 MHz, chloroform-d) δ 8.35 (1H, br. s.), 7.08-7.17 (1 H, m), 6.98-7.06 (1H, m), 6.95 (1H, d, J=1.98 Hz), 2.93 (2H, t, J=7.59 Hz), 2.49-2.68 (2H, m). Mass spectrum m/z 226, 228 (M+H)+.
Reference: [1] Patent: US2010/160303, 2010, A1, . Location in patent: Page/Page column 36
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2452 - 2468
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 9005 - 9017
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