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Chemistry
Heterocyclic Building Blocks
Azetidines
tert-Butyl 3-(4-bromophenoxy)azetidine-1-carboxylate
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Azetidines
Aryls Bromides Amides Ethers Aliphatic Heterocycles

[ CAS No. 960402-39-5 ] {[proInfo.proName]}

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Chemical Structure| 960402-39-5
Chemical Structure| 960402-39-5
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Product Details of [ 960402-39-5 ]

CAS No. :960402-39-5 MDL No. :MFCD17215696
Formula : C14H18BrNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 328.20 Pubchem ID :-
Synonyms :

Safety of [ 960402-39-5 ]

Signal Word: Class:
Precautionary Statements: UN#:
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Application In Synthesis of [ 960402-39-5 ]

* 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 [ 960402-39-5 ]

[ 960402-39-5 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 460-00-4 ]
  • [ 141699-55-0 ]
  • [ 960402-39-5 ]
YieldReaction ConditionsOperation in experiment
46% With potassium tert-butylate; In tetrahydrofuran; at 20 - 70℃; Preparation 131; 3-(4-Bromo-phenoxy)-azetidine-l-carboxylic acid tert-bvAyl ester; Add dropwise potassium tert-butoxide in THF (34.6 mL, 34.6 mmol) to a solution oip- bromofluorobenzene (6.1 g, 34.6 mmol) in THF (144 mL) and 3-hydroxy-azetidine-l- carboxylic acid tert-butyl ester (5.0 g, 28.9 mmol) at RT. Heat the mixture at 70 0C overnight. Cool the mixture to RT, quench with water, dilute with Et2O, and wash once with saturated NH4Cl. Back extract the aqueous with Et2O, dry the combined organics over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 25% EtOAc/hexane to give 4.4 g (46%) of the title compound. LC-MS/ES m/z (81Br) 274 [M -tertBu+H]+.
19% With potassium tert-butylate; In tetrahydrofuran; at 20 - 70℃; for 4.0h; Combine l-bromo-4-fluorobenzene (10.1 g, 57.7 mmol) and tert-butyl 3- hydroxyazetidine-1-carboxylate (5.0 g, 28.9 mmol) in THF (144 mL) and stir at room temperature. Add slowly potassium tert-butoxide (75.7 mL, 57.7 mmol, IM in THF). Heat the mixture at 70 0C for 4 h. Monitor the reaction completion via gas chromatography. Cool the mixture to room temperature and quench with water. Dilute the mixture with ether. Wash the organic portion with saturated NH4Cl. Back extract the aqueous with ether. Dry the combined organics with Na2SO4, filter, and concentrate. Purify the material by flash chromatography using 5-10% EtOAc/hexanes to give 1.84 g (19% yield) of the title compound as a white solid.
Reference： [1]Patent: WO2007/146758,2007,A2 .Location in patent: Page/Page column 82
[2]Patent: WO2008/76562,2008,A1 .Location in patent: Page/Page column 51
  • 2
  • [ 106-41-2 ]
  • [ 141699-55-0 ]
  • [ 960402-39-5 ]
YieldReaction ConditionsOperation in experiment
79.5% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 110℃; for 5.0h;Inert atmosphere; A mixture of tert-butyl 3-hydroxyazetidine-1-carboxylate (200 mg, 1.15 mmol), 4-bromophenol (240 mg, 1.39 mmol), triphenylphosphine (398 mg, 1.50 mmol) and DIAD (202 mg, 1.39 mmol) in anhydrous THF (5 mL) was heated to 110 C. and stirred under nitrogen for 5 hours. The reaction mixture was concentrated in vacuo to give a brown residue, which was purified by flash chromatography (petroleum ether/ethyl acetate 10:1 to 4:1) to give tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate (300 mg, 79.5%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.39 (d, 2H), 6.72 (d, 2H), 4.84 (m, 1H), 4.28 (m, 2H), 3.99 (m, 2H), 1.44 (s, 9H).
72.6% With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 110℃; for 1.0h;Sealed tube; Microwave irradiation; To a solution of 4-bromophenol, 15, (130 mg, 0.76 mmol) in toluene (10 mL)was added tert-butyl 3-hydroxyazetidine-1-carboxylate, R-24, (130 mg, 0.76mmol), PPh3 (240 mg, 0.91 mmol), DIAD (186 mg, 0.91 mmol). The sealedvial was irradiated in the microwave on a Biotage Smith Synthesis at 110 00 for 1 h. The reaction mixture was quenched into water, extracted with DCM, dried with anhydrous Na2504, concentrated to give the crude product which was purified by prep-TLC to give the reagent KR-26 (180 mg, 72.6%) as apale yellow solid. ESI-MS (Mi-i): 328.1 calc. for C14H18BrNO3: 327.0.
Reference： [1]Patent: US2013/267493,2013,A1 .Location in patent: Paragraph 0730; 0731
[2]Patent: WO2014/131855,2014,A1 .Location in patent: Page/Page column 60
  • 3
  • [ 960402-39-5 ]
  • [ 954224-25-0 ]
YieldReaction ConditionsOperation in experiment
100% With trifluoroacetic acid; In dichloromethane; at 20℃; To a solution of <strong>[960402-39-5]tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate</strong> (300 mg, 0.90 mmol) in CH2Cl2 (5 mL) was added TFA (5 mL). The mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo to give 3-(4-bromophenoxy)azetidine (207 mg, 100%) as a yellow oil.
Reference： [1]Patent: US2013/267493,2013,A1 .Location in patent: Paragraph 0732
  • 4
  • [ 960402-39-5 ]
  • [ 1467060-01-0 ]
Reference： [1]Patent: US2013/267493,2013,A1
  • 5
  • [ 960402-39-5 ]
  • [ 1467060-02-1 ]
Reference： [1]Patent: US2013/267493,2013,A1
  • 6
  • [ 960402-39-5 ]
  • C20H17ClN2O3 [ No CAS ]
Reference： [1]Patent: US2013/267493,2013,A1
  • 7
  • [ 960402-39-5 ]
  • [ 1467057-37-9 ]
Reference： [1]Patent: US2013/267493,2013,A1
  • 8
  • [ 1126-09-6 ]
  • [ 960402-39-5 ]
  • ethyl 1-[4-(1-tert-butoxycarbonylazetidin-3-yl)oxyphenyl]piperidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.1% With bis(tri-t-butylphosphine)palladium(0); caesium carbonate; In 1,4-dioxane; at 120℃; for 6.0h;Inert atmosphere; To a suspension of KR-26 (94 mg, 0.29 mmol) and compound ethylpiperidine-4 carboxylate, R-23, (50 mg, 0.32 mmol) in 1,4-dioxane (10 mL)was added 0s2003 (284 mg, 0.87 mmol), Pd(tBu)3P (45 mg, 0.087 mmol). The mixture was stirred at 120 00 under N2 for 6 h. The resulting mixture was cooled to room temperature and concentrated under vacuo. The mixture was quenched into water, extracted with DOM, dried with anhydrous Na2504,concentrated to give the crude product which was purified by prep-TLC (PE:EA=1 :0 to 3:1) to give KR-27 (75 mg, 64.1%) as a pale yellow solid. ESIMS (Mi-i ):405.2 calc. for 022H32N205: 404.2.
Reference： [1]Patent: WO2014/131855,2014,A1 .Location in patent: Page/Page column 60
  • 9
  • 1-benzhydryl-3-(4-bromophenoxy)azetidine [ No CAS ]
  • [ 960402-39-5 ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 10
  • [ 24424-99-5 ]
  • 3-(4-bromophenoxy)azetidine hydrochloride [ No CAS ]
  • [ 960402-39-5 ]
YieldReaction ConditionsOperation in experiment
74% To a stirred solution of 3-(4-bromophenoxy)azetidine hydrochloride (443 mg, 1.67mmol) in methanol (4 mL) was added N,N-diisopropylethylamine (585 mu, 3.35 mmol). After 15 min, di- tert-butyl dicarbonate (731 mg, 3.35 mmol) was added and the reaction was stirred overnight. The reaction was quenched by addition of water then extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2S04) and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 0% to 20% EtOAc in heptane) to afford the title compound as a white solid (428 mg, 74%). MS (ISP): 274.1 ([{81Br}M-C4 +H]+), 272.1 ([{79Br}M-C4H8 +H]+).
Reference： [1]Patent: WO2016/30310,2016,A1 .Location in patent: Page/Page column 50
  • 11
  • [ 960402-39-5 ]
  • tert-butyl 3-[4-[(4-chlorobenzoyl)amino]phenoxy]azetidine-1-carboxylate [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 12
  • [ 960402-39-5 ]
  • N-(4-(azetidin-3-yloxy)phenyl)-4-chlorobenzamide hydrochloride [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 13
  • [ 960402-39-5 ]
  • [ 643087-88-1 ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 14
  • [ 960402-39-5 ]
  • tert-butyl 3-(4-(2-(trifluoromethyl)pyrimidin-4-ylamino)phenoxy)azetidine-1-carboxylate [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 15
  • [ 960402-39-5 ]
  • N-[4-(azetidin-3-yloxy)phenyl]-2-(trifluoromethyl)pyrimidin-4-amine hydrochloride [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 16
  • [ 960402-39-5 ]
  • tert-butyl 3-[ 4-[(3-cyclopropyl-1H-pyrazole-5-carbonyl)amino]phenoxy]azetidine-1-carboxylate [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 17
  • [ 960402-39-5 ]
  • N-(4-(azetidin-3-yloxy)phenyl)-3-cyclopropyl-1H-pyrazole-5-carboxamide [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 18
  • [ 960402-39-5 ]
  • tert-butyl 3-[4-[[2-(2,2,2-trifluoroethoxy)pyrimidine-5-carbonyl]amino]phenoxy]azetidine-1-carboxylate [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 19
  • [ 960402-39-5 ]
  • N-(4-(azetidin-3-yloxy)phenyl)-2-(2,2,2-trifluoroethoxy)pyrimidine-5-carboxamide 2,2,2-trifluoroacetic acid [ No CAS ]
Reference： [1]Patent: WO2016/30310,2016,A1
  • 20
  • [ 1013-88-3 ]
  • [ 960402-39-5 ]
  • tert-butyl 3-(4-(diphenylmethyleneamino)phenoxy)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 90℃;Inert atmosphere; A microwave vial was charged with tert-butyl 3-(3-bromophenoxy)azetidine-l-carboxylate (274 mg, 835 muiotaetaomicron), benzophenone imine (66 mg, 918 muiotaetaomicron, CAS 1013-88-3 ), sodium tert-butoxide (128 mg, 1.34 mmol), rac-2,2'-bis(diphenylphosphino)-l,l'-binaphthyl (52.0 mg, 83.5 muiotaetaomicron), Pd2(dba)3 (22.9 mg, 25.0 muiotaetaomicron) and toluene (2 mL). The resulting mixture was degassed for 5 min by bubbling nitrogen through the reaction mixture. The reaction was heated to 90 C overnight and then filtered directly through a pad of dicalite. The filter cake was rinsed with EtOAc and the filtrate concentrate in vacuo. The crude residue was purified by flash chromatography (silica gel, 0% to 30% EtOAc in heptane) to afford the title compound (321 mg, 89%) as a light yellow oil. MS (ISP): 429.1 ([M+H]+).
Reference： [1]Patent: WO2016/30310,2016,A1 .Location in patent: Page/Page column 50
  • 21
  • [ 960402-39-5 ]
  • [ 191162-39-7 ]
  • tert-butyl 3-(4-(quinolin-3-yl)phenoxy)azetidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 15.0h;Inert atmosphere; A solution of tert-butyl 3 -(4-bromophenoxy)azetidine- 1 -carboxylate (1.5 g, 4.57 mmol), quinolin-3-boronic acid (948 mg, 5.5 mmol) and Na2CO3 (1.2 g, 11.42 mmol) in1,4-dioxane (60 mL) and water (15 mL) was degassed by argon for 15 mm. Tetrakis(triphenylphosphine) palladium(0) (264 mg, 0.23 mmol) was then added under argon atmosphere and reaction mixture was heated at 100 C for 15 h. The reaction mixture was cooled to RT and filtered through Celite pad, washed with ETOAc. Filtrate was washed with water and brine, dried over Na2504, filtered and concentrated. The cmde product was purified by column chromatography (50% EtOAc-Hexane) to afford tert-butyl 3-(4-(quinolin-3- yl)phenoxy)azetidine-1-carboxylate (950 mg, 55%). Analysis: LCMS (ESI): 377 (M+1); ?H NMR (400 MHz, DMSO-d6) oe: 9.22 (d, J 2.3 Hz, 1H), 8.58 (d, J 2.5 Hz, 1H), 8.03 (d, J 8.3 Hz, 2H), 7.84 (d, J= 8.2 Hz, 2H), 7.81-7.70 (m, 1H), 7.63 (t, J= 7.5 Hz, 1H), 7.02 (d, J8.2 Hz, 2H), 5.08 (m, 1H), 4.35 (t, J= 7.9 Hz, 2H), 3.84 (dd, J= 10.1, 4.0 Hz, 2H), 1.40 (s, 9H).
Reference： [1]Patent: WO2016/205633,2016,A1 .Location in patent: Paragraph 00643
  • 22
  • [ 106-41-2 ]
  • [ 141699-58-3 ]
  • [ 960402-39-5 ]
YieldReaction ConditionsOperation in experiment
71% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 18.0h; To tert-butyl 3-((methylsulfonyl)oxy)azetidine-1-carboxylate (7 g, 0.027 mol) and Cs2CO3 (10.9g, 0.033mo1) in DMF (200 mL) was added 4-bromophenol (4.82g,0.027mo1). The reaction was heated to 80 C for 18 h, and then cooled to RT. Ice water was added to the reaction mixture when a white solid tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate was obtained which was filtered, washed with water and dried (6.5 g, 7 1%). Analysis: ?H NMR (400 MI-Tz, DMSO-d6) oe: 7.50-7.41 (m, 2H), 6.85-6.76 (m, 2H), 5.0-4.96 (m, 1H), 4.32-4.23 (m, 2H), 3.77 (m, 2H), 1.38 (s, 9H); LCMS (ESI): 328 (M+1).
Reference： [1]Patent: WO2016/205633,2016,A1 .Location in patent: Paragraph 00642
  • 23
  • [ 960402-39-5 ]
  • 1-(3-(4-(quinolin-3-yl)phenoxy)azetidin-1-yl)propan-1-one [ No CAS ]
Reference： [1]Patent: WO2016/205633,2016,A1
  • 24
  • [ 960402-39-5 ]
  • 3-(4-(azetidin-3-yloxy)phenyl)quinoline hydrochloride [ No CAS ]
Reference： [1]Patent: WO2016/205633,2016,A1
  • 25
  • [ 960402-39-5 ]
  • [ 98-80-6 ]
  • C20H23NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 1.0h;Inert atmosphere; General procedure: Into a microwave vessel were added tert-butyl 3-((4-bromobenzyl)oxy)azetidine-1-carboxylate (200 mg, 0.58 mmol), (4-methoxyphenyl)boronic acid (177 mg, 1.16 mmol), K2CO3 (240 mg, 1.74 mmol), dioxane (8 mL) and water (2 mL). Argon gas was passed through the mixture for 10 minutes and then tetrakis(triphenylphosphine)palladium(0) (6.7 mg 0.0058 mmol) and the argon flow continued for 5 additional minutes. Then, the vessel was sealed and microwaved at 100 C for1 h. The mixture was diluted with EtOAc (30 mL) and washed with water and brine. The organics extracts were dried over anhydrous MgSO4. The solvents were removed under vacuum and the residue was purified on silica gel (Biotage; eluting solvents hexanes: EtOAc 4/1 ratio) to afford tert-butyl 3-((4'-methoxy-[1,1'-biphenyl]-4-yl)methoxy)azetidine-1-carboxylate as viscous oil
Reference： [1]Bioorganic and Medicinal Chemistry,2020,vol. 28
  • 26
  • [ 960402-39-5 ]
  • 3-([1,1'-biphenyl]-4-yloxy)azetidine-1-carbonitrile [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2020,vol. 28
  • 27
  • [ 960402-39-5 ]
  • C15H15NO*C2HF3O2 [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2020,vol. 28

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