Alternatived Products of [ 138865-41-5 ]
Product Details of [ 138865-41-5 ]
| CAS No. : | 138865-41-5 |
MDL No. : | MFCD27756646 |
| Formula : |
C17H13BrO
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | GOORTGQVODJZGU-UHFFFAOYSA-N |
| M.W : |
313.19
|
Pubchem ID : | 378873 |
| Synonyms : |
|
Safety of [ 138865-41-5 ]
Application In Synthesis of [ 138865-41-5 ]
* 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 [ 138865-41-5 ]
- 1
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[ 607-58-9 ]
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[ 138865-41-5 ]
- 2
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[ 571-57-3 ]
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[ 100-39-0 ]
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[ 138865-41-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 93% |
With potassium carbonate In acetonitrile for 14h; Heating; |
|
| 71.2% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; |
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With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 2h; |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; |
2.I s:v;aI:1?xIs of I(benzj1oay4-brotnonaphtisaiene (3)
To a solution of 2 (7 g, 31,4 mmol) in DMF, K2,C03 (8.9 g. 6444 mmol) was added ‘followed hysiow addition of berizyl bromide (3.98 mL, 33.5 mmol). Thereaction mixture was stirred at RI’ and monitored using TLC. After completIon, reaction was quenched with brine and the residue was extracted using ethyl acetate and washed with water. The combined organic layer was cined over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained solid was purified by column chromatography (Hex: EtOAc, 98:2). |
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With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; |
1.F
To a solution of compound 61 (2 g, 8.96 mmo1, 1 equiv.), and compound 62 (2.13 mL, 17.93 mmo1, 2 equiv.) in anhydrous DMF (10 mL) was added K2CO3(2.48 g, 17.93 mmo1, 2 equiv.) at 0 °C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by water (10 mL). The aqueous phase was extracted with ethyl acetate (3 x 10 mL) and the organic phase was combined, dried over anhydrous Na2SO4, and concentrated. The product was separated by CombiFlash using silica gel as the stationary phase. |
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With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; |
3
[00338] To a solution of compound 61 (2 g, 8.96 mmol, 1 equiv.), and compound 62 (2.13 mL, 17.93 mmol, 2 equiv.) in anhydrous DMF (10 mL) was added K2CO3 (2.48 g, 17.93 mmol, 2 equiv.) at 0 °C. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched by water (10 mL). The aqueous phase was extracted with ethyl acetate (3 x 10 mL) and the organic phase was combined, dried over anhydrous Na2SO4, and concentrated. The product was separated by CombiFlash using silica gel as the stationary phase. |
Reference：
[1]Lowe III, John A.; Qian, Weimin; Drozda, Susan E.; Volkmann, Robert A.; Nason, Deane; Nelson, Robert B.; Nolan, Charles; Liston, Dane; Ward, Karen; Faraci, Steve; Verdries, Kim; Seymour, Pat; Majchrzak, Michael; Villalobos, Anabella; White, W. Frost
[Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1575 - 1586]
[2]Current Patent Assignee: ROCHE HOLDING AG; RQX PHARMACEUTICALS INC - WO2018/149419, 2018, A1
Location in patent: Paragraph 00632
[3]Location in patent: experimental part
Veljkovic, Jelena; Uzelac, Lidija; Molcanov, Kresimir; Mlinaric-Majerski, Kata; Kralj, Marijeta; Wan, Peter; Basaric, Nikola
[Journal of Organic Chemistry, 2012, vol. 77, # 10, p. 4596 - 4610]
[4]Current Patent Assignee: GODAVARI BIOREFINERIES - WO2018/193476, 2018, A2
Location in patent: Page/Page column 36; 37; 38
[5]Current Patent Assignee: ARROWHEAD RESEARCH CORP - WO2021/86995, 2021, A1
Location in patent: Paragraph 0239; 0247;0251
[6]Current Patent Assignee: ARROWHEAD RESEARCH CORP - WO2022/56269, 2022, A1
Location in patent: Paragraph 00338
- 3
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[ 571-57-3 ]
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[ 620-05-3 ]
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[ 138865-41-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 79% |
With potassium carbonate In acetonitrile at 20 - 60℃; |
|
- 4
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[ 571-57-3 ]
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[ 100-44-7 ]
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[ 138865-41-5 ]
| Yield | Reaction Conditions | Operation in experiment |
| 94% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; |
1
22.3 g (100 mmols) of 4-bromo-1-naphthol was dissolved in 440 ml of dimethylformamide, and to which 20.7 g (150 mmols) potassium carbonate and 13.9 g (110 mmols) of benzyl chloride were added to react them at 50° C. After 3 hours have passed, 440 ml of toluene and 880 ml of water were added thereto, the organic layer was washed with water, the solvent was removed and, thereafter, the reaction product was refined by chromatography (solvent chloroform) using silica gel to obtain a white solid material of a 1-benzyloxy-4-bromonaphthalene represented by the following formula in an amount of 29.4 g (94 mmols, yield: 94%) |
| 94% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h; |
j0180] 22.3 Grams (100 mmols) of 4-bromo-l-naphthol was dissolved in 440 ml of dimethylformamide, and to which 20.7 g (150 mmols) potassium carbonate and 13.9 g (110 mmols) of benzyl chloride were added to react them at 50° C.10181] After 3 hours have passed, 440 ml of toluene and880 ml of water were added thereto, the organic layer waswashed with water, the solvent was removed and, thereafier,the reaction product was refined by chromatography (solventchloroform) using silica gel to obtain a white solid material ofa 1 -benzyloxy-4-bromonaphthalene represented by the following formula in an amount of 29.4 g (94 mmols, yield:94%). j0182] In the following formula, Bn is a benzyl group which is the protection group (hereinafier the same). |
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