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Chemistry
Heterocyclic Building Blocks
Benzodioxans
5-Bromo-2,3-dihydro-1,4-benzodioxane
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Benzodioxans
Bromides

[ CAS No. 58328-39-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 58328-39-5
Chemical Structure| 58328-39-5
Chemical Structure| 58328-39-5
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Quality Control of [ 58328-39-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 58328-39-5 ]

Product Details of [ 58328-39-5 ]

CAS No. :58328-39-5 MDL No. :MFCD03095029
Formula : C8H7BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NGOZRIZXELGVHK-UHFFFAOYSA-N
M.W : 215.04 Pubchem ID :18787268
Synonyms :

Calculated chemistry of [ 58328-39-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.01
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 2.33
Log Po/w (WLOGP) : 2.22
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.31

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.194 mg/ml ; 0.000902 mol/l
Class : Soluble
Log S (Ali) : -2.36
Solubility : 0.946 mg/ml ; 0.0044 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.111 mg/ml ; 0.000515 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.33

Safety of [ 58328-39-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58328-39-5 ]

* 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 [ 58328-39-5 ]

[ 58328-39-5 ] Synthesis Path-Downstream   1~48

  • 1
  • [ 58328-39-5 ]
  • [ 57260-71-6 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium t-butanolate;Inert atmosphere; Microwave irradiation; General procedure: [00159] A solution of aryl halide (1.0eq), Pd catalyst [Pd(OAc)2 or Pd2(dba)3 (0511) (tris(dibenzylideneacetone) dipalladium(O)) ] (0.1 eq), phosphine ligand (XPhos (2- dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), or XantPhos (4,5- (0512) Bis(diphenylphosphino)-9,9-dimethylxanthene), or DavePhos (2-Dicyclohexylphosphino-2'- (N,N-dimethylamino)biphenyl)) (0.3eq), sodium tert-butoxide (1.5eq), and the appropriate amine or aniline (1.0-1.5eq) in dry 1 ,4-dioxane or toluene was purged with nitrogen for 15 min and the mixture was heated to 80-1 10 C for 2-16 h thermally or in microwave reactor. Reaction was monitored by LCMS. On consumption of starting material the reaction was filtered to remove any inorganic salts and the filtrate was concentrated under reduced pressure to yield the crude material which was purified by column chromatography or prep HPLC.
Reference： [1]Patent: WO2019/145718,2019,A1 .Location in patent: Paragraph 00297-00298; 00159
[2]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222
  • 2
  • [ 1692-15-5 ]
  • [ 58328-39-5 ]
  • [ 222992-07-6 ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 3
  • [ 58328-39-5 ]
  • 2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-6-methyl-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 4
  • [ 58328-39-5 ]
  • 2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-5-methyl-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 5
  • [ 58328-39-5 ]
  • cis-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)-3,6-dihydro-2H-pyridin-1-yl]indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 6
  • [ 58328-39-5 ]
  • trans-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl) 3,6-dihydro-2H-pyridin-1-yl] indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 7
  • [ 58328-39-5 ]
  • trans-2-[4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)-piperid-1-yl]indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 8
  • [ 58328-39-5 ]
  • (1S,2S)-2-(4-Benzofuran-7-yl-piperidin-1-yl)-5-fluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 9
  • [ 58328-39-5 ]
  • 2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-6-fluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 10
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-6-methyl-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 11
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-5-methyl-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 12
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-6-fluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 13
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2H-pyridin-1-yl]-5-fluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 14
  • [ 58328-39-5 ]
  • 6-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-6,7-dihydro-5<i>H</i>-indeno[5,6-<i>d</i>][1,3]dioxol-5-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 15
  • [ 58328-39-5 ]
  • 2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-5,6-dimethoxy-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 16
  • [ 58328-39-5 ]
  • 2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-3,6-dihydro-2<i>H</i>-pyridin-1-yl]-5,6-difluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 17
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-5,6-dimethoxy-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 18
  • [ 58328-39-5 ]
  • (1S,2S)-2-[4-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-5,6-difluoro-indan-1-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 19
  • [ 58328-39-5 ]
  • 6-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-piperidin-1-yl]-6,7-dihydro-5<i>H</i>-indeno[5,6-<i>d</i>][1,3]dioxol-5-ol [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 20
  • [ 58328-39-5 ]
  • 4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)-1-(1-oxoindan-2-yl)pyridinium bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 21
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(5-methyl-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 22
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(6-methyl-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 23
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(6-fluoro-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 24
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(5-fluoro-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 25
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(5,6-dimethoxy-1-oxo-indan-2-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 26
  • [ 58328-39-5 ]
  • 1-(5,6-difluoro-1-oxo-indan-2-yl)-4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 27
  • [ 58328-39-5 ]
  • 4-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-1-(5-oxo-6,7-dihydro-5<i>H</i>-indeno[5,6-<i>d</i>][1,3]dioxol-6-yl)-pyridinium; bromide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 165 - 176
  • 28
  • [ 58328-39-5 ]
  • [ 98224-03-4 ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 2219 - 2222
  • 29
  • [ 58328-39-5 ]
  • [ 87474-15-5 ]
YieldReaction ConditionsOperation in experiment
69% To 2,3-Methylenedioxy-bromobenzene (2.43 g, 0.012 mole) in 20 mL of THF at -78 C., was added slowly n-BuLi (4.84 mL, 2.5 M in hexane) was slowly added. The reaction was stirred at for 1 hour and then SO2 (g) was bubbled through the solution for 10 minutes. The reaction was warmed to room temperature, poured into 200 mL of ether, filtered, and dried under vacuum, to afford the lithio salt (2.1 g, 91 % yield). The lithio salt (2.1 g) was dissolved in 20 mL of glacial acetic acid at 15 C. NCS (1.61 g, 0.013 moles) was added over 15 minutes. The mixture was warmed to room temperature and stirred for 1 hour. The solvent was removed under vacuum and the residue was dissolved in 100 mL of methylene chloride, washed with 50 mL of sat. sodium bicarbonate, dried over magnesium sulfate and the solvent was removed under vacuum. The residue was chromatographed on 100 g of silica gel, eluted with methylene chloride and the fractions were combined and evaporated under reduced pressure to yield 2,3-methylenedioxy-benzene sulphonyl chloride (1.7 g, 69 % yield).
Reference： [1]Patent: US6342504,2002,B1 .Location in patent: Page column 123-124
[2]Patent: WO2020/127960,2020,A1
[3]Patent: WO2021/249969,2021,A1
  • 30
  • [ 14381-51-2 ]
  • [ 106-93-4 ]
  • [ 58328-39-5 ]
YieldReaction ConditionsOperation in experiment
45% With potassium fluoride; In DMF (N,N-dimethyl-formamide); at 135℃; for 3h; To <strong>[14381-51-2]2,3-dihydroxy-bromobenzene</strong> (3.0 g, 0.16 mole), KF (4.63 g, 0.080 mole), DMF (15 ML was added CH2Br2 (4.13 g, 0.024 moles).. This suspension was heated to 135° C. for 3 hours, cooled and filtered.. The filtrate was poured into 200 ML of ether and washed with water, 1 N KOH and brine.. The organic layer was dried over magnesium sulfate, filtered and the solvent removed under vacuum, to yield 2,3-Methylenedioxy-bromobenzene (1.45 g, 45 percent yield).
Reference： [1]Patent: US6342504,2002,B1 .Location in patent: Page column 123
  • 31
  • [ 3612-20-2 ]
  • [ 58328-39-5 ]
  • N-benzyl-4-hydroxy-4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With n-butyllithium; In water; toluene; (a) N-benzyl-4-hydroxy-4-(2,3-dihydrobenzo[1,4]dioxin-5-yl)piperidine A toluene solution (10 ml) of <strong>[58328-39-5]5-bromo-2,3-dihydrobenzo[1,4]dioxin</strong> (10 mmol) was stirred under argon at 0 C. and was treated with the dropwise addition of n-butyllithium (10 mmol) over ten minutes. After stirring for a further twenty minutes a solution of 1-benzyl-4-piperidone in toluene (10 mmol in 10 ml) was added dropwise over five minutes. Stirring was continued for two hours, at which point water (100 ml) was added and the product extracted into ethyl acetate (4*50 ml). The combined organics were washed with water (2*50 ml), brine (75 ml) and dried (MgSO4). Filtration and concentration in vacuo gave an oil. Purification by column chromatography (SiO2, EtOAc) gave the required product in 61% yield.
With n-butyllithium; In tetrahydrofuran; hexane; water; Stage A 1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine 23.3 ml of a 1.6 M solution of butyllithium in hexane are added dropwise to a solution, previously cooled to -60 C., of 8 g of 5-bromo-1,4-benzodioxane in 400 ml of tetrahydrofuran. When the addition is complete, the mixture is stirred at -60 C. for 5 minutes and a solution of 8 g of 1-benzylpiperid-4-one in 100 ml of tetrahydrofuran is then added dropwise. The mixture is stirred for 2 hours at -40 C. and then for 2 hours at ambient temperature before hydrolyzing using 80 ml of water. The organic phase is separated off and the aqueous phase is extracted with twice 100 ml of dichloromethane. The combined organic phases are washed once using 20 ml of water and dried over magnesium sulfate. The solvents are evaporated under vacuum and the product obtained in the crude stage is chromatographed on 520 g of silica (70-230 mesh), eluding using a 98:2 (V/V) dichloromethane/methanol mixture. Yield: 72% Proton nuclear magnetic resonance spectrum (solvent CDCl3): 2.05 ppm m 2H; 2.1 ppm m 2H; 2.55 ppm m 2H; 2.75 ppm m 2H; 3.6 ppm s 2H; 4.25 ppm m 4H; 6.8 ppm m 3H; 7.1-7.4 ppm m 5H
Reference： [1]Patent: US5763460,1998,A
[2]Patent: US5240942,1993,A
  • 32
  • [ 58328-39-5 ]
  • [ 87474-16-6 ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; acetic acid; EXAMPLE 15 1,4-Benzodioxan-5-sulfonamide To a solution of 43.6 g 5-bromo-1,4-benzodioxan (prepared according to the procedures of S. Cabiddu et al., Synthesis, loc. cit.) and in 400 ml tetrahydrofuran -70 under nitrogen was added dropwise 127 ml of n-butyllithium (1.6N in hexane). The temperature was maintained at -70 C. with dry ice/acetone cooling during the addition. The reaction mixture was stirred 0.5 hour at -70 C. Excess sulfur dioxide was bubbled through the reaction mixture, kept at -60 to -70 C. with cooling until no further exotherm was noted. The reaction mixture was stirred at -70 C. for 2.5 hours, warmed to room temperature, stirred overnight, and 10 ml isopropyl alcohol is added. The reaction mixture was concentrated in vacuo and crystallized from ether/tetrahydrofuran to give a solid. The solid was added to 150 ml acetic acid and the resultant mixture was cooled to 20 C. A slurry of 20.5 g of N-chlorosuccinimide in 125 ml acetic acid was added portionwise with cooling to maintain the reaction mixture between 20-25 C. The reaction mixture was stirred 3 hours at ambient temperature and the solvent was removed under reduced pressure to give an oil. The oil was dissolved in methylene chloride and washed with water. The organic phase was dried and the solvent removed under reduced pressure to give an oil which was dissolved in 300 ml ether and cooled to 10 C. Excess ammonia (anhy.) was bubbled through the reaction mixture using ice bath cooling. The reaction mixture was warmed to ambient temperature, stirred for 1 hour, and 100 ml ether added. The reaction mixture was washed with water, dried, and concentrated in vacuo to give a solid, m.p. 114-117 C., IR(mull). 1 H-NMR (DMSO-d6): 4.3 (s, 4H); and 6.7-7.6 (m, 5H).
With N-chloro-succinimide; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; acetic acid; EXAMPLE 15 1,4-Benzodioxan-5-sulfonamide To a solution of 43.6 g 5-bromo-1,4-benzodioxan (prepared according to the procedures of S. Cabiddu et al., Synthesis, loc. cit.) and in 400 ml tetrahydrofuran -70 under nitrogen was added dropwise 127 ml of n-butyllithium (1.6N in hexane). The temperature was maintained at -70 C. with dry ice/acetone cooling during the addition. The reaction mixture was stirred 0.5 hour at -70 C. Excess sulfur dioxide was bubbled through the reaction mixture, kept at -60 to -70 C. with cooling until no further exotherm was noted. The reaction mixture was stirred at -70 C. for 2.5 hours, warmed to room temperature, stirred overnight, and 10 ml isopropyl alcohol is added. The reaction mixture was concentrated in vacuo and crystallized from ether/tetrahydrofuran to give a solid. The solid was added to 150 ml acetic acid and the resultant mixture was cooled to 20 C. A slurry of 20.5 of N-chlorosuccinimide in 125 ml acetic acid was added portionwise with cooling to maintain the reaction mixture between 20-25 C. The reaction mixture was stirred 3 hours at ambient temperature and the solvent was removed under reduced pressure to give an oil. The oil was dissolved in methylene chloride and washed with water. The organic phase was dried and the solvent removed under reduced pressure to give an oil which was dissolved in 300 ml ether and cooled to 10 C. Excess ammonia (anhy.) was bubbled through the reaction mixture using ice bath cooling. The reaction mixture was warmed to ambient temperature, stirred for 1 hour, and 100 ml ether added. The reaction mixture was washed with water, dried, and concentrated in vacuo to give a solid, m.p. 114-117 C., IR(mull). 1 H-NMR (DMSO-d6): 4.3 (s, 4H); and 6.7-7.6 (m, 5H).
Reference： [1]Patent: US4659368,1987,A
[2]Patent: US4502882,1985,A
  • 33
  • [ 1426806-31-6 ]
  • [ 58328-39-5 ]
  • [ 1426803-86-2 ]
YieldReaction ConditionsOperation in experiment
33 mg With tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 100℃; for 0.5h;Microwave irradiation; To a mixture of N-(3,5-dichloro-4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)phenyl)-2-(4- (ethylsulfonyl)phenyl)acetamide (200 mg, see step 1 for synthesis of Example 203), 5-bromo-2,3- dihydrobenzo[Z>][l,4]dioxine (129 mg), 2M sodium carbonate solution (0.602 mL) and xi-tert- butylphosphine, tetrafluoroboric acid salt (46.6 mg) in 1 ,4-dioxane (2 mL) was added Pd2(dba)3 (36.8 mg) under nitrogen. The mixture was stirred and heated in the microwave at 100C for half an hour. After cooling, the mixture was diluted with water, and extracted with EA for three times. The organic layer was dried and filtered through silica gel, and evaporated in vacuo. The residue was purified by MDAP to afford N-(3,5-dichloro-4-(2,3-dihydrobenzo[i][l,4]dioxin-5-yl)phenyl)-2-(4- (ethylsulfonyl)phenyl)acetamide (33 mg). Ή-NMR (400 MHz, DMSO-^) δ ppm 1.1 1 (t, J= 7.3 Hz, 3H), 3.29 (m, 2H), 3.85 (s, 2H), 4.17 (m; 2H), 4.24 (m, 2H), 6.66 (dd, 3= 6.5 Hz, 2.5 Hz, 1H), 6.91 (m, 2H), 7.62 (d, /= 8.3 Hz, 2H), 7.78 (s, 2H), 7.87 (d, J= 8.3 Hz, 2H), 10.64 (s, 1H); 19F-NM (376 MHz, DMSO- ) δ ppm -69.10, -71.10, -74.10; MS(ES+) m/z 506 (MH+).
Reference： [1]Patent: WO2013/29338,2013,A1 .Location in patent: Page/Page column 200; 201
  • 34
  • [ 110-85-0 ]
  • [ 58328-39-5 ]
  • [ 98224-03-4 ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10601 - 10618
  • 35
  • [ 58328-39-5 ]
  • 5-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)-butoxy)-2-ethylbenzo[d]thiazole [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10601 - 10618
  • 36
  • [ 58328-39-5 ]
  • 5-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)-butoxy)-2-isopropylbenzo[d]thiazole [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10601 - 10618
  • 37
  • [ 58328-39-5 ]
  • 5-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)-butoxy)-N-methylbenzo[d]thiazol-2-amine [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10601 - 10618
  • 38
  • [ 58328-39-5 ]
  • 5-(4-(4-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazin-1-yl)-butoxy)-2-methylbenzo[d]thiazole [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10601 - 10618
  • 39
  • [ 1196152-34-7 ]
  • [ 58328-39-5 ]
  • 2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridin-4-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% [00237] A solution of 5-bromo-2,3-dihydro-benzo[1,4]dioxine (1.0 eq, 4.65 mmol), PdCl2(dtbpf) ([1, 1 '-bis(di-fe/f-butylphosphino)ferrocene] dichloropalladium(ll)) (0.1 eq, 0.46 mmol), KOAc (2.5 eq, 1 1.6 mmol), and bis(pinacolato)diboron (1.5 eq, 10.2 mmol) in dioxane (10 ml_) was purged with N2 for 10 min and the mixture was heated to 120 C for 3 h. Then, 2-bromo-6-methoxy-pyridin-4-amine (1.0 eq, 4.65 mmol), Pd(PPh3)4 (0.1 eq, 0.46 mmol), K2CO3 (2.0 eq, 9.30 mmol) and H2O (1 ml_) were added. The reaction was purged with N2 for 10 min and the mixture was heated to 110 C for 2.5 h. the mixture was cooled to RT then the solvent was removed. The dark residue was dissolved in ethyl acetate and filtered over celite. The compound in this organic layer was directly washed with water, brine, dried over magnesium sulphate, filtered and the reaction was concentrated in vacuo. The compound was purified by column chromatography eluting with dichloromethane then increasing the polarity with 0-5 % MeOH. Then the compound was purified by preparative HPLC-MS to afford 2-(2,3- dihydro-1,4-benzodioxin-5-yl)-6-methoxy-pyridin-4-amine (780 mg, 65 %) as a white solid. AnalpH2_MeOH_QC_V1, Rt: 3.93 min, m/z 259.3 [M+H]+ AnalpH9_MeOH_QC_V1, Rt: 6.46 min, m/z 259.3 [M+H]+
Reference： [1]Patent: WO2019/145718,2019,A1 .Location in patent: Paragraph 00236-00237
  • 40
  • [ 58328-39-5 ]
  • (R)-3-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridin-4-ylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester [ No CAS ]
Reference： [1]Patent: WO2019/145718,2019,A1
  • 41
  • [ 58328-39-5 ]
  • {4-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridin-4-ylcarbamoyl]cyclohexyl}carbamic acid tert-butyl ester [ No CAS ]
Reference： [1]Patent: WO2019/145718,2019,A1
  • 42
  • [ 58328-39-5 ]
  • (R)-pyrrolidine-3-carboxylic acid [2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridin-4-yl]amide [ No CAS ]
Reference： [1]Patent: WO2019/145718,2019,A1
  • 43
  • [ 58328-39-5 ]
  • 3-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridin-4-yl]-1-methyl-1-(1-methylpiperidin-4-yl)-urea [ No CAS ]
Reference： [1]Patent: WO2019/145718,2019,A1
  • 44
  • [ 58328-39-5 ]
  • (6-methoxypyridin-2-yl)boronic acid [ No CAS ]
  • 2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate; In 1,4-dioxane; water; at 110℃; for 1h;Inert atmosphere; [00234] A solution of <strong>[58328-39-5]5-bromo-2,3-dihydro-benzo[1,4]dioxine</strong> (90 mg, 0.42mmol, 1.Oeq), PdC idtbpf) ([1, T-bis(di-tert-butylphosphino)ferrocene] dichloropalladium(ll)) (27 mg, 0.042 mmol, 0.1 eq), Na2C03 (133 mg, 2.2eq) and 6-methoxypyridine-2-boronic acid (128 mg, 0.84mmol, 2. Oeq) in 9:1 1,4-dioxane:H20 (5mL) was purged with N2 for 15 min and the mixture was heated to 110 C for 1 h. Once complete the reaction was filtered to remove any inorganic salts and the filtrate was concentrated in vacuo to yield the crude material which was purified by prep HPLC to give 2-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-6-methoxy-pyridine as an off-white solid (56.5 mg, 55%) AnalpH2_MeOH_QC_V1 : Rt: 7.77 min, m/z 244.3 [M+H]+ AnalpH9_MeOH_QC_V1 : Rt: 7.86 min, m/z 244.3 [M+H]+
Reference： [1]Patent: WO2019/145718,2019,A1 .Location in patent: Paragraph 00233-00234
  • 45
  • [ 58328-39-5 ]
  • 4-[2-[2-(2,3-dihydro-1,4-benzodioxine-5-sulfonamido)phenyl]ethynyl]benzoic acid [ No CAS ]
Reference： [1]Patent: WO2020/127960,2020,A1
[2]Patent: WO2021/249969,2021,A1
  • 46
  • [ 58328-39-5 ]
  • methyl 4-[2-[2-(2,3-dihydro-1,4-benzodioxine-5-sulfonamido)phenyl]ethynyl]benzoate [ No CAS ]
Reference： [1]Patent: WO2020/127960,2020,A1
[2]Patent: WO2021/249969,2021,A1
  • 47
  • [ 150-60-7 ]
  • [ 58328-39-5 ]
  • 5-(benzylsulfanyl)-2,3-dihydro-1,4-benzodioxine [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% (Note:“-C-” stands for“-CH2-”) In a 100-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, 5-bromo-2,3-dihydro-1 ,4-benzodioxine (1.6 g, 6.70 mmol, 1 eq, 90%) was dissolved in THF (30 ml_). This was followed by the addition of s-BuLi (12 ml_, 1.87 mmol, 1.3M in THF) dropwise with stirring at -78C and stirring was continued for 30 min at the given temperature. Then [(benzyldisulfanyl)methyl]benzene (2.2 g, 8.48 mmol, 1.3 eq, 95%) was added. After complete addition the reaction was stirred for 1 h at room temperature. The reaction was quenched by the addition of water. The resulting solution was extracted with 100 ml_ of ethyl acetate and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.5 g (78%) of 5- (benzylsulfanyl)-2,3-dihydro-1 ,4-benzodioxine as yellow oil.
78% In a 100-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, <strong>[58328-39-5]5-bromo-2,3-dihydro-1,4-benzodioxine</strong> (1.6 g, 6.70 mmol, 1 eq, 90%) was dissolved in THF (30 mL). This was followed by the addition of s-BuLi (12 mL, 1.87 mmol, 1.3M in THF) dropwise with stirring at -78C and stirring was continued for 30 min at the given temperature. Then [(benzyldisulfanyl)methyl]benzene (2.2 g, 8.48 mmol, 1.3 eq, 95%) was added. After complete addition the reaction was stirred for 1H at room temperature. The reaction was quenched by the addition of water. The resulting solution was extracted with 100 mL of ethyl acetate and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.5 g (78%) of 5-(benzylsulfanyl)-2,3-dihydro-1,4-benzodioxine as yellow oil.
78% In a 100-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, <strong>[58328-39-5]5-bromo-2,3-dihydro-1,4-benzodioxine</strong> (1.6 g, 6.70 mmol, 1 eq, 90%) was dissolved in THF (30 mL). This was followed by the addition of s-BuLi (12 mL, 1.87 mmol, 1.3M in THF) dropwise with stirring at -78C and stirring was continued for 30 min at the given temperature. Then [(benzyldisulfanyl)methyl]benzene (2.2 g, 8.48 mmol, 1.3 eq, 95%) was added. After complete addition the reaction was stirred for 1H at room temperature. The reaction was quenched by the addition of water. The resulting solution was extracted with 100 mL of ethyl acetate and the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1.5 g (78%) of 5-(benzylsulfanyl)-2,3-dihydro-1,4-benzodioxine as yellow oil.
Reference： [1]Patent: WO2020/127960,2020,A1 .Location in patent: Page/Page column 132-133
[2]Patent: WO2021/249969,2021,A1 .Location in patent: Page/Page column 139
[3]Patent: WO2021/249969,2021,A1 .Location in patent: Page/Page column 139
  • 48
  • [ 73183-34-3 ]
  • [ 58328-39-5 ]
  • 2-(2,3-dihydro-1,4-benzodioxin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere; A stirred solution of <strong>[58328-39-5]5-bromo-2,3-dihydrobenzo[b][1,4]dioxine</strong> (0.2 g, 0.93 mmol, 1 eq), bis(pinacolato)diborane (0.282 g, 1.116 mmol, 1.2 eq) and potassium acetate (0.273 g, 2.7 mmol, 3 eq) in 1,4-dioxane (20 mL) was deoxygenated with argon gas for 10 min. PdCl2(dppf).DCM (0.075 g, 0.093 mmol. 0.1 eq) was added and the reaction mixture was stirred at 90C for another 16 h. After completion (monitored by TLC), the reaction mixture was filtered through a celite bed. The filtrate was concentrated under reduced pressure to afford the cmde material which was used in the next step without any purification.
Reference： [1]Patent: WO2021/144439,2021,A1 .Location in patent: Page/Page column 37

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