125769-77-9

Basic information

• Product Name: Tributyl(4,5-dihydrofuran-2-yl)tin
• Synonyms: Tributyl(4,5-dihydrofuran-2-yl)stannane;Tributyl(4,5-dihydrofuran-2-yl)tin;Tributyl(4,5-dihydrofuran-2-yl)stannane 97%
• CAS NO: 125769-77-9
• Molecular Formula: C₁₆H₃₂OSn
• Molecular Weight: 359.13468
• Product Categories: Chemical Synthesis;Organometallic Reagents;Organotin;Organotins
• Mol File: 125769-77-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 361.4±52.0 °C(Predicted)
• Flash Point: >110°C
• Appearance: /
• Density: 1.128g/mLat 25℃
• Refractive Index: n20/D 1.493
• CAS DataBase Reference: Tributyl(4,5-dihydrofuran-2-yl)tin(CAS DataBase Reference)
• NIST Chemistry Reference: Tributyl(4,5-dihydrofuran-2-yl)tin(125769-77-9)
• EPA Substance Registry System: Tributyl(4,5-dihydrofuran-2-yl)tin(125769-77-9)

Safety Data

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61
• RIDADR: UN 2788 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 125769-77-9(Hazardous Substances Data)

Usage

Uses

Tributyl(4,5-dihydrofuran-2-yl)stannane is an organotin compound (or organostannane), which can be used as a reactant: In the palladium-catalyzed Stille coupling reaction to prepare furan-containing aryl derivatives by reacting with various aryl halides. To synthesize 2,3-dihydro-5-(2-methylphenyl)furan by coupling with 2-iodotoluene in the presence of a palladium catalyst. In the chemoselective preparation of hexatrienes by the tandem palladium-catalyzed Heck and Stille coupling of bromohexenyl triflates and acrylates.

Synthetic route

2,3-dihydro-2H-furan (1191-99-7) + tributyltin chloride (1461-22-9) → tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9)

Conditions	Yield
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -60 - 0℃; for 1h; Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -60 - 0℃; for 1.5h; Stage #3: With water; ammonium chloride In tetrahydrofuran; pentane	100%
Stage #1: 2,3-dihydro-2H-furan With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -78℃; for 1h;

2,3-dihydro-2H-furan (1191-99-7) + stannane (7440-31-5) + 4-iodobenzo[b]thiophene-2-carboxamidine hydrochloride (149732-36-5) + tributyltin chloride (1461-22-9) + methyl 4-iodobenzo[b]thiophene-2-carboxylate (146137-85-1) → tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9)

Conditions	Yield
With tert.-butyl lithium; lithium chloride; bis(triphenylphosphine)palladium(II)-chloride In N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide	99%

tributylstannyl trifluoromethanesulfonate (68725-14-4) + 1-butyn-4-ol (927-74-2) → tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9)

Conditions	Yield
With hexacarbonyl molybdenum; triethylamine In diethyl ether Irradiation (UV/VIS); N2-atmosphere; irradn. (20 min), alkynyl alcohol and Sn-compd. addn., stirring (18 h); evapn., chromy. (SiO2, pentane / Et2O / 1% Et2NH);	64%

2-acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (912573-57-0) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 2-acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (912573-91-2)

Conditions	Yield
With triethylamine; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 18h; Stille Coupling; Heating / reflux;	86%

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-iodo-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine (142189-90-0) → 3-(4,5-Dihydro-furan-2-yl)-1-(tetrahydro-pyran-2-yl)-7-(tetrahydro-pyran-2-yloxy)-1H-pyrazolo[4,3-d]pyrimidine

Conditions	Yield
With triphenyl-arsane; palladium diacetate In acetonitrile at 25℃; for 8h; other substrates;	85%
With triphenyl-arsane; palladium diacetate In acetonitrile at 25℃; for 8h;	85%

ortho-methylphenyl iodide (615-37-2) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 5-o-Tolyl-2,3-dihydro-furan (132093-52-8)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In tetrahydrofuran for 2h; Heating;	84%

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione (148875-57-4) → 2-benzoyl-4-(2,3-dihydrofuran-5-yl)-4-hydroxy-3-(1-piperidinyl)-2-cyclobuten-1-one

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h;	73%

(4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (179248-66-9) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → (4-Benzyloxy-phenyl)-(6-(2,3-dihydrofuran-5-yl)-quinazolin-4-yl)-amine (202196-44-9)

Conditions	Yield
bis(triphenylphosphine)palladium(II)-chloride In 1,4-dioxane; 2-Methylpentane; ethyl acetate	72%

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 2,4-dimethoxy-5-iodopyrimidine (52522-99-3) → 5-(4,5-Dihydro-furan-2-yl)-2,4-dimethoxy-pyrimidine

Conditions	Yield
With triphenyl-arsane; palladium diacetate In acetonitrile at 40℃; for 8h;	65%

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 4-iodo-1-[(4-methylphenyl)sulfonyl]-1H-imidazole (163854-63-5) → N-tosyl-4-[2'-(4,5-dihydro)furanyl]imidazole

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 110℃; for 2h; Stille Cross Coupling; Microwave irradiation; Inert atmosphere;	65%

(Z)-methyl but-2-enoate (4358-59-2) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → (E)-3-(4,5-Dihydro-furan-2-yl)-acrylic acid methyl ester (132093-58-4)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In tetrahydrofuran	64%

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-tert-butyl-4-methylcyclobut-3-ene-1,2-dione (114094-90-5) → 4-acetoxy-2-tert-butyl-4-[5'-(2',3'-dihydrofuranyl)]-3-methyl-2-cyclobutenone

Conditions	Yield
Stage #1: tributyl-(4,5-dihydro-furan-2-yl)-stannane With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Metallation; Stage #2: 3-tert-butyl-4-methylcyclobut-3-ene-1,2-dione In tetrahydrofuran; hexane at -78℃; for 1h; Addition; Stage #3: acetic anhydride In tetrahydrofuran; hexane at -78℃; for 1.5h; Acetylation;	54%

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → (6R,7R)-3-(4,5-dihydrofuran-2-yl)-7-phenylacetamido-ceph-3-em-4-carboxylic acid (153565-73-2)

Conditions	Yield
	49%

o-bromobenzyl alcohol (18982-54-2) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 4,5-dihydro-3H,3'H-spiro[furan-2,1'-isobenzofuran] (139697-84-0) + [2-(4,5-Dihydro-furan-2-yl)-phenyl]-methanol (139697-82-8)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In acetonitrile Heating;	A 12% B 35%

1-bromovinylbenzene (98-81-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 5-(1-Phenyl-vinyl)-2,3-dihydro-furan (132100-57-3)

Conditions	Yield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In tetrahydrofuran Heating;

2-bromophenylethyl alcohol (1074-16-4) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 2-[2-(4,5-Dihydro-furan-2-yl)-phenyl]-ethanol (139697-83-9)

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

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-Benzoyl-4-(1-piperidinyl)-3-cyclobutene-1,2-dione (148875-57-4) → 4-acetoxy-2-benzoyl-4-(2,3-dihydrofuran-5-yl)-3-(1-piperidinyl)-2-cyclobuten-1-one

Conditions	Yield
With n-butyllithium 1.) THF, pentane, -78 deg C, 10 min, 2.) warmed to room temperature; Yield given. Multistep reaction;

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-benzoyl-4-(tert-butylamino)-3-cyclobutene-1,2-dione (172979-17-8) → 4-acetoxy-2-benzoyl-3-(tert-butylamino)-4-(2,3-dihydrofuran-5-yl)-2-cyclobuten-1-one

Conditions	Yield
With n-butyllithium 1.) THF, pentane, -78 deg C, 10 min, 2.) warmed to room temperature; Yield given. Multistep reaction;

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-acetyl-4-(N,N-dibenzylamino)-3-cyclobutene-1,2-dione (172979-18-9) → 4-acetoxy-2-acetyl-3-(N,N-dibenzylamino)-4-(2,3-dihydrofuran-5-yl)-2-cyclobuten-1-one

Conditions	Yield
With n-butyllithium 1.) THF, pentane, -78 deg C, 10 min, 2.) warmed to room temperature; Yield given. Multistep reaction;

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 4-tert-butyl-3-isopropoxy-3-cyclobutene-1,2-dione (73287-85-1) → acetic acid 3-tert-butyl-1-(4,5-dihydro-furan-2-yl)-2-isopropoxy-4-oxo-cyclobut-2-enyl ester

Conditions	Yield
Stage #1: tributyl-(4,5-dihydro-furan-2-yl)-stannane With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Metallation; Stage #2: 4-tert-butyl-3-isopropoxy-3-cyclobutene-1,2-dione In tetrahydrofuran; hexane at -78℃; Addition; Stage #3: acetic anhydride In tetrahydrofuran; hexane at -78℃; Acetylation;

acetic anhydride (108-24-7) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 3-methyl-4-trimethylsilyl-3-cyclobutene-1,2-dione (154473-78-6) → acetic acid 1-(4,5-dihydro-furan-2-yl)-2-methyl-4-oxo-3-trimethylsilanyl-cyclobut-2-enyl ester + Acetic acid (E)-1-(4,5-dihydro-furan-2-yl)-2-methyl-4-oxo-3-trimethylsilanyl-buta-1,3-dienyl ester

Conditions	Yield
Stage #1: tributyl-(4,5-dihydro-furan-2-yl)-stannane With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 0.5h; Metallation; Stage #2: 3-methyl-4-trimethylsilyl-3-cyclobutene-1,2-dione In tetrahydrofuran; hexane at -78℃; for 2h; Addition; Stage #3: acetic anhydride In tetrahydrofuran; hexane at -78℃; for 1.5h; Acetylation; Title compound not separated from byproducts;

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + 1-bromo-2-trifluoromethanesulfonyloxycyclohexene (213340-08-0) → 5-(2-bromo-cyclohex-1-enyl)-2,3-dihydro-furan

Conditions	Yield
With zinc(II) chloride; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 40℃; for 19h; Stille coupling;

tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + benzoyl chloride (98-88-4) → 2-Benzoyl-4,5-dihydrofuran (161144-22-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 3h;

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) + bis(dibenzylideneacetone)-palladium(0) (32005-36-0) → 4-Methoxybenzyl (6R,7R)-3-(4,5-dihydrofuran-2-yl)-7-phenylacetamido-ceph-3-em-4-carboxylate (153565-68-5)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one; hexane

9-iodo-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (1571143-31-1) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 9-(4,5-dihydrofuran-2-yl)-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (1571145-75-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 150℃; for 1.5h; Microwave irradiation;	543 mg
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 150℃; for 1.5h; Microwave irradiation;	543 mg

2-(4-ethyl-1H-imidazol-1-yl)-9-iodo-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (1571146-13-8) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 9-(4,5-dihydrofuran-2-yl)-2-(4-ethyl-1H-imidazol-1-yl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one (1604830-43-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 150℃; for 1.5h;	254 mg
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 150℃; for 1.5h;	254 mg

(4-bromo-2-furyl)[4-({(1R,3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-[(triisopropylsilyl)oxy]cyclopentyl}amino)pyrimidin-5-yl]methanone + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → [4-({(1R,3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyI)-4-[(triisopropylsilyl)oxy]cyclopentyl}amino)pyrimidin-5-yl](4,5-dihydro-2,3'-bifuran-5'-yl)methanone

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine In 1,4-dioxane at 110℃; Inert atmosphere;	44 mg

4-bromo-6-chloro-3-pyridazineamine (446273-59-2) + tributyl-(4,5-dihydro-furan-2-yl)-stannane (125769-77-9) → 6-chloro-4-(4,5-dihydrofuran-2-yl)pyridazin-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In N,N-dimethyl-formamide at 90℃; Inert atmosphere; Sealed tube;	0.36 g

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 1461-22-9 tributyltin chloride 
• 68725-14-4 tributylstannyl trifluoromethanesulfonate 
• 927-74-2 3-Butyn-1-ol 
• 7440-31-5 stannane 
• 149732-36-5 4-iodobenzo[b]thiophene-2-carboxamidine hydrochloride 
• 146137-85-1 methyl 4-iodobenzo[b]thiophene-2-carboxylate 

Downstream Products

• 132093-52-8 5-o-Tolyl-2,3-dihydro-furan 
• 1571145-75-9 9-(4,5-dihydrofuran-2-yl)-2-(3-methoxyphenyl)-7,8-dihydro-[1,4]diazepino[7,1-a]isoquinolin-5(4H)-one 
• 153565-68-5 4-Methoxybenzyl (6R,7R)-3-(4,5-dihydrofuran-2-yl)-7-phenylacetamido-ceph-3-em-4-carboxylate 
• 912573-91-2 2-acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester 
• 202196-44-9 (4-Benzyloxy-phenyl)-(6-(2,3-dihydrofuran-5-yl)-quinazolin-4-yl)-amine 
• 161144-22-5 2-Benzoyl-4,5-dihydrofuran 
• 139697-83-9 2-[2-(4,5-Dihydro-furan-2-yl)-phenyl]-ethanol 
• 139697-84-0 4,5-dihydro-3H,3'H-spiro[furan-2,1'-isobenzofuran] 
• 139697-82-8 [2-(4,5-Dihydro-furan-2-yl)-phenyl]-methanol 
• 132100-57-3 5-(1-Phenyl-vinyl)-2,3-dihydro-furan 

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