189035-22-1

Usage

Uses

Used in Pharmaceutical Industry:
6-BROMO-2,3-DIHYDRO-BENZOFURAN is used as a key intermediate in the synthesis of 2-alkylamino nicotinamide analogs. These analogs are known to act as orally active ghrelin receptor (ghrelinR) inverse agonists, which have potential therapeutic applications in treating various medical conditions related to ghrelin receptor dysregulation.
Application Reason:
The ghrelin receptor plays a crucial role in regulating various physiological processes, including appetite, energy balance, and growth hormone secretion. Modulating the activity of this receptor with inverse agonists can help in the development of treatments for obesity, cachexia, and other related disorders. By using 6-BROMO-2,3-DIHYDRO-BENZOFURAN as a starting material, chemists can synthesize novel ghrelinR inverse agonists with improved pharmacological properties, such as better oral bioavailability and reduced side effects.

InChI:InChI=1/C8H7BrO/c9-7-2-1-6-3-4-10-8(6)5-7/h1-2,5H,3-4H2

Synthetic route

1,4-dibromo-2-(2-bromoethoxy)benzene (377091-18-4) → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 4h;	94%
With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1h; Inert atmosphere;	85%
With n-butyllithium In tetrahydrofuran; benzene at -78℃; for 1h; Inert atmosphere;	85%

1,4-dibromo-2-hydroxyethoxybenzene (377091-17-3) → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
Stage #1: 1,4-dibromo-2-hydroxyethoxybenzene With phosphorus tribromide In toluene at 90℃; for 2.5h; Heating / reflux; Stage #2: With sodium hydroxide In water; toluene at 20℃; Stage #3: With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.5h;	40%
Multi-step reaction with 2 steps 1: phosphorus tribromide / toluene / 10 h / 90 °C 2: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: phosphorus tribromide / toluene / 2.5 h / 20 - 90 °C 2: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C / Inert atmosphere View Scheme

2,3-Dihydrobenzofuran (496-16-2) → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
With potassium hydroxide; bromine; potassium bromide at 20℃;

2-trimethylstannyl-1,3-cyclohexadiene + Br2 -solution → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
In n-heptane; dichloromethane; ethyl acetate

2,5-dibromophenol (28165-52-8) → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / 40 h / 80 °C 2: n-butyllithium / hexane; tetrahydrofuran / 4 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 4 h / 80 °C 2: n-butyllithium / tetrahydrofuran / 3 h / -100 °C View Scheme

2,5-dibromofluorobenzene (1435-52-5) → 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1-methyl-pyrrolidin-2-one; potassium tert-butylate / 100 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 10 h / 90 °C 3: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 100 °C / Inert atmosphere 2: phosphorus tribromide / toluene / 10 h / 90 °C 3: n-butyllithium / tetrahydrofuran; benzene / 1 h / -78 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium tert-butylate; 1-methyl-pyrrolidin-2-one / 15 h / 20 - 100 °C 2: phosphorus tribromide / toluene / 2.5 h / 20 - 90 °C 3: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C / Inert atmosphere View Scheme

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 5,6-dibromo-2,3-dihydro-1-benzofuran (1102467-17-3)

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h;	93%
With N-Bromosuccinimide In acetonitrile at 20℃;

potassium cyanide + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → C9H7NO

Conditions	Yield
Stage #1: potassium cyanide With acetic acid In ethylene glycol at 20℃; Sealed tube; Stage #2: 6-bromo-2,3-dihydro-1-benzofuran With P(t-Bu)3 Palladacycle Gen. 3; potassium acetate In 1,4-dioxane; water at 60℃; for 16h; Sealed tube;	93%

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine (496047-46-2) → 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine (721965-55-5)

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran Stage #2: 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-oxocyclopenta-1,3-dieno[2,1-b]pyridine In tetrahydrofuran at -78℃; for 1h; Grignard reaction;	89%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 2,3-dihydro-1-benzofuran-6-carbaldehyde (55745-96-5)

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In 2-methyltetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran; hexane at -78℃; for 2h;	85%
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran; hexane at -75℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 0.75h;	79%
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	52%

2-ethylhexyl 3-sulfanylpropanoate (50448-95-8) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 2-ethylhexyl 3-(2,3-dihydro-1-benzofuran-6-ylthio)propanoate (1156468-65-3)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 10h; Inert atmosphere;	83%
With N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 10h;	33%

pinacol vinylboronate (75927-49-0) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 6-vinyl-2,3-dihydrobenzofuran

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 105℃; for 16h;	79.4%

formaldehyd (50-00-0) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → (2,3-dihydrobenzofuran-6-yl)methanol (1083168-69-7)

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; pentane at -74 - 20℃; Inert atmosphere;	74%

tributyl(1-ethoxyvinyl)stannane (97674-02-7) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 1-(2,3-dihydrobenzofuran-6-yl)ethan-1-one (374706-07-7)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In toluene at 90℃; for 16h;	73.7%

oxirene (157-18-6) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 2-(2,3-dihydrobenzofuran-6-yl)ethan-1-ol

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With iodine; magnesium In tetrahydrofuran at 20 - 70℃; for 1h; Inert atmosphere; Stage #2: oxirene In tetrahydrofuran at 20℃; for 2h;	64.3%

Dimethyldisulphide (624-92-0) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 6-(methylthio)-2,3-dihydro-1-benzofuran (1102467-20-8)

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.5h; Stage #2: Dimethyldisulphide In tetrahydrofuran; hexanes for 1h;	62%

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + 2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine (464170-04-5) → (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid (464170-05-6)

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #3: With sulfuric acid In 1,4-dioxane; water at 100℃; for 1.5h;	60%

2-(6-trifluoromethyl-pyridin-3-yl)-ethylamine (765287-34-1) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → (2,3-dihydro-benzofuran-6-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (1201195-88-1)

Conditions	Yield
With caesium carbonate; copper(l) iodide; 2-acetylcyclohexanone In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	52%

tert-butyl 2-oxopyrrolidine-1-carboxylate (85909-08-6) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → tert-butyl (4-(2,3-dihydrobenzofuran-6-yl)-4-oxobutyl)carbamate

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium; lithium chloride In tetrahydrofuran; ethylene dibromide at 65℃; for 2h; Stage #2: tert-butyl 2-oxopyrrolidine-1-carboxylate In tetrahydrofuran; ethylene dibromide at -78℃; for 2h;	37%

3-(((4-methoxybenzyl)(methyl)amino)methyl)-2-methylbenzofuran-7-ol + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 1-(7-((2,3-dihydrobenzofuran-6-yl)oxy)-2-methylbenzofuran-3-yl)-N-(4-methoxybenzyl)-N-methylmethanamine

Conditions	Yield
With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid In dimethyl sulfoxide at 110℃; for 16h;	27%

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + Benzyl-(6-bromo-5-{(E)-2-[(4S,5S)-4-methoxymethyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-2-yl]-vinyl}-pyridin-2-yl)-isopropyl-amine → (S)-3-[6-(Benzyl-isopropyl-amino)-2-bromo-pyridin-3-yl]-3-(2,3-dihydro-benzofuran-6-yl)-propionic acid

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: Benzyl-(6-bromo-5-{(E)-2-[(4S,5S)-4-methoxymethyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-2-yl]-vinyl}-pyridin-2-yl)-isopropyl-amine In tetrahydrofuran; hexane at -78℃; Stage #3: With sulfuric acid In 1,4-dioxane; water at 100℃;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + (S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-isopropyl-oxazolidin-2-one (494841-72-4) → (S)-3-[3-(2-Chloro-pyridin-3-yl)-3-(2,3-dihydro-benzofuran-6-yl)-propionyl]-4-isopropyl-oxazolidin-2-one

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran at 70℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.333333h; Stage #3: (S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-isopropyl-oxazolidin-2-one In tetrahydrofuran at -78℃; for 1h; Michael addition;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + (S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-phenyl-oxazolidin-2-one (494841-70-2) → (S)-3-[3-(2-Chloro-pyridin-3-yl)-3-(2,3-dihydro-benzofuran-6-yl)-propionyl]-4-phenyl-oxazolidin-2-one

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran at 70℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.333333h; Stage #3: (S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-phenyl-oxazolidin-2-one In tetrahydrofuran at -78℃; for 1h; Michael addition;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + (4S,5R)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one (494841-71-3) → (4S,5R)-3-[3-(2-Chloro-pyridin-3-yl)-3-(2,3-dihydro-benzofuran-6-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran at 70℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.333333h; Stage #3: (4S,5R)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4-methyl-5-phenyl-oxazolidin-2-one In tetrahydrofuran at -78℃; for 1h; Michael addition;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + (R)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-5,5-dimethyl-4-phenyl-oxazolidin-2-one (494841-73-5) → (R)-3-[3-(2-Chloro-pyridin-3-yl)-3-(2,3-dihydro-benzofuran-6-yl)-propionyl]-5,5-dimethyl-4-phenyl-oxazolidin-2-one

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran at 70℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.333333h; Stage #3: (R)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-5,5-dimethyl-4-phenyl-oxazolidin-2-one In tetrahydrofuran at -78℃; for 1h; Michael addition;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + 2-chloro-3-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine (494841-80-4) → 2-Chloro-3-{1-(2,3-dihydro-benzofuran-6-yl)-2-[(4S,5S)-4-methoxymethyl-5-(4-methylsulfanyl-phenyl)-4,5-dihydro-oxazol-2-yl]-ethyl}-pyridine

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2-chloro-3-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine In tetrahydrofuran; hexane at -78℃;	76 % Chromat.

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + (4R,5S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4,5-diphenyl-oxazolidin-2-one (494841-74-6) → (4R,5S)-3-[3-(2-Chloro-pyridin-3-yl)-3-(2,3-dihydro-benzofuran-6-yl)-propionyl]-4,5-diphenyl-oxazolidin-2-one

Conditions	Yield
Stage #1: 6-bromo-2,3-dihydro-1-benzofuran With magnesium In tetrahydrofuran at 70℃; for 2h; Stage #2: With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at 5℃; for 0.333333h; Stage #3: (4R,5S)-3-[(E)-3-(2-Chloro-pyridin-3-yl)-acryloyl]-4,5-diphenyl-oxazolidin-2-one In tetrahydrofuran at -78℃; for 1h; Michael addition;

ethyl acrylate (140-88-5) + 6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → (E)-3-(2,3-Dihydro-benzofuran-6-yl)-acrylic acid ethyl ester

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile at 90℃;

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 5-(2,3-dihydro-benzofuran-6-yl)-7-(2-hydroxy-4-methoxy-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Mg / tetrahydrofuran 1.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 4-(dimethylamino)pyridine / CHCl3 / 1 h / 20 °C 3.1: 189 g / H2; NaHCO3 / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr 4.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C View Scheme

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → (5RS,6RS,7SR)-7-(2-hydroxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Mg / tetrahydrofuran 1.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 4-(dimethylamino)pyridine / CHCl3 / 1 h / 20 °C 3.1: 189 g / H2; NaHCO3 / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr View Scheme

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → 5-(2,3-dihydro-benzofuran-6-yl)-7-(4-methoxy-2-vinyl-phenyl)-6,7-dihydro-5H-[1]pyrindine-6-carboxylic acid tert-butyl ester

Conditions

Yield

Multi-step reaction with 6 steps 1.1: Mg / tetrahydrofuran 1.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 4-(dimethylamino)pyridine / CHCl3 / 1 h / 20 °C 3.1: 189 g / H2; NaHCO3 / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr 4.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 5.1: 172 g / 4-(dimethylamino)pyridine / CHCl3 / 0.5 h / 0 °C 6.1: dichloro[bis(triphenylphosphine)]palladium; LiCl / dimethylformamide / 4 h / 125 °C 6.2: 112 g / KF / dimethylformamide; H2O; ethyl acetate / 0.5 h / 20 °C View Scheme

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) → (5RS,6SR,7SR)-7-(2-hydroxymethyl-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine

Conditions

Yield

Multi-step reaction with 8 steps 1.1: Mg / tetrahydrofuran 1.2: 89 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 4-(dimethylamino)pyridine / CHCl3 / 1 h / 20 °C 3.1: 189 g / H2; NaHCO3 / Pd(OH)2/C / tetrahydrofuran; ethanol / 45 h / 20 °C / 760 Torr 4.1: potassium tert-butoxide / tetrahydrofuran; 2-methyl-propan-2-ol / 0.33 h / 0 °C 5.1: 172 g / 4-(dimethylamino)pyridine / CHCl3 / 0.5 h / 0 °C 6.1: dichloro[bis(triphenylphosphine)]palladium; LiCl / dimethylformamide / 4 h / 125 °C 6.2: 112 g / KF / dimethylformamide; H2O; ethyl acetate / 0.5 h / 20 °C 7.1: OsO4; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O / 12 h / 20 °C 8.1: NaIO4; 4-methylmorpholine N-oxide / tetrahydrofuran; H2O / 0.33 h / 0 °C 8.2: 84.2 g / NaBH4 / tetrahydrofuran; H2O / 0.33 h / 20 °C View Scheme

Upstream product

• 1435-52-5 2,5-dibromofluorobenzene 
• 28165-52-8 2,5-dibromophenol 
• 377091-18-4 1,4-dibromo-2-(2-bromoethoxy)benzene 
• 377091-17-3 1,4-dibromo-2-hydroxyethoxybenzene 
• 496-16-2 2.3-dihydrobenzofuran 

Downstream Products

• 917815-18-0 {4-[(2R,3R)-3-[2-(2,3-dihydro-benzofuran-6-yl)-2-oxo-ethylsulfanyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetic acid tert-butyl ester 
• 721965-55-5 7-(2-benzyloxy-4-methoxyphenyl)-6-tert-butoxycarbonyl-5-(2,3-dihydrobenzo[b]furan-6-yl)-5-hydroxy-5H-cyclopenta[b]pyridine 
• 917815-08-8 {4-[(2R,3R)-3-[2-(2,3-dihydro-benzofuran-6-yl)-2-oxo-ethylsulfanyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetic acid 
• 374706-07-7 1-(2,3-dihydrobenzofuran-6-yl)ethan-1-one 
• 1083168-69-7 (2,3-dihydrobenzofuran-6-yl)methanol 

Relevant academic research and scientific papers

5,5-DIFLUORO- AND 5-FLUORO-5-METHYL-C-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS

The present invention is directed to 5,5-difluoro- and 5-fluoro-5-methyl-C-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.

Heterocyclic compound

The present invention relates to compound (I) or a salt thereof which has a ROR γ t inhibitory action. wherein each symbol is as defined in the specification.

COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF

The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.

COMPOUND OF CAMPTOTHECIN AND PREPARATION AND USE THEREOF

The present disclosure relates to a compound of formula I, a pharmaceutical composition thereof and the use thereof as an anti-tumor drug.

Orally active ghrelin receptor inverse agonists and their actions on a rat obesity model

A series of 2-alkylamino nicotinamide analogs was prepared as orally active ghrelin receptor (ghrelinR) inverse agonists. Starting from compound 1, oral bioavailability was improved by modifying metabolically unstable sites and reducing molecular weight. Brain-permeable compound 33 and compound 24 with low brain permeability were tested in rat models of obesity; 30 mg/kg of compound 33 suppressed weight gain. PK/PD analysis revealed that the anti-obesity effect of ghrelinR inverse agonists depends on their brain concentrations.

COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM

Described herein are compounds and pharmaceutical compositions containing such compounds, which modulate the activity of store-operated calcium (SOC) channels. Also described herein are methods of using such SOC channel modulators, alone and in combination with other compounds, for treating diseases or conditions that would benefit from inhibition of SOC channel activity.

ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

COMPOUNDS AS HSP90 INHIBITORS

The invention provides novel compounds of formula (I) wherein: one of the a, b, c or d members is a nitrogen atom and the remaining members are carbon atoms; and R3 is a radical selected from the group consisting of: —S—R14 and —CH2—R15. The compounds of formula (I) are useful for treating diseases mediated by a heat shock protein 90 (Hsp 90)

INHIBITORS OF TNFα, PDE4 AND B-RAF, COMPOSITIONS THEREOF AND METHODS OF USE THEREWITH

Provided herein are compounds having TNFα and/or PDE4 and/or B-RAF inhibitory activity, and compositions thereof. In particular, provided herein are compounds of the formula (I) and pharmaceutically acceptable salts, solvates, hydrates, clathrates, stereoisomers, polymorphs and prodrugs thereof, wherein Ar, R1, R2, R3, R4, n and Z are as described herein. Further provided herein are methods for treating or preventing various diseases and disorders by administering to a patient one or more TNFα and/or PDE4 and/or B-RAF inhibitors. In particular, provided herein are methods for preventing or treating cancer, inflammatory disorders, cognition and memory disorders and autoimmune disorders, or one or more symptoms thereof by administering to a patient one or more TNFα and/or PDE4 and/or B-RAF inhibitors.

Nonpeptide αvβ3 Antagonists. 8. In Vitro and in Vivo Evaluation of a Potent αvβ3 Antagonist for the Prevention and Treatment of Osteoporosis

3(S)-(6-Methoxypyridin-3-yl)-3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8] -naphthyridin-2-yl)propyl]-imidazolidin-1-yl}propionic acid 6 was identified as a potent and selective antagonist of the αvβ3 receptor. This compound has an excellent in vitro profile (IC50 = 0.08 nM), a significant unbound fraction in human plasma (12%), and good pharmacokinetics in rat, dog, and rhesus monkey. On the basis of the efficacy shown in three in vivo models of bone turnover, the compound was selected for clinical development. To support the ongoing metabolism and safety studies, a novel strategy was employed in which a series of oxidized derivatives of 6 were prepared by exposure of 6 (or the methyl ester) to chemical oxidizing agents. These products proved useful in the identification of active metabolites generated by either in vitro or in vivo metabolism.