33733-73-2

Basic information

• Product Name: 3-Bromothioanisole
• Synonyms: M-BROMO(METHYLTHIO)BENZENE;M-BROMOTHIOANISOLE;3-BROMOPHENYL METHYL SULFIDE;3-BROMOTHIOANISOLE;1-BROMO-3-(METHYLTHIO)BENZENE;3-Bromophenyl methyl sulphide;3-Bromothioanisol/3-Bromophenyl methyl sulphide;m-bromothioanisole(MBTA)
• CAS NO: 33733-73-2
• Molecular Formula: C₇H₇BrS
• Molecular Weight: 203.1
• EINECS: 1308068-626-2
• Product Categories: Miscellaneous;Aromatics Compounds;Aromatics;Sulfur & Selenium Compounds
• Mol File: 33733-73-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 124-125 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Pale-Yellow Liquid
• Density: 1.51 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.007mmHg at 25°C
• Refractive Index: n20/D 1.628(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive: Stench
• BRN: 2078598
• CAS DataBase Reference: 3-Bromothioanisole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromothioanisole(33733-73-2)
• EPA Substance Registry System: 3-Bromothioanisole(33733-73-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-37-26
• RIDADR: UN 3334
• WGK Germany: 3
• HazardClass: IRRITANT, STENCH
• Hazardous Substances Data: 33733-73-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H7BrOS/c1-9-6-3-2-4-7(5-6)10-8/h2-5H,1H3

Synthetic route

3-Bromothiophenol (6320-01-0) + methyl iodide (74-88-4) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With potassium carbonate In acetone for 4h; Heating;	100%
Stage #1: 3-Bromothiophenol With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: methyl iodide In methanol at 20℃; Further stages.;	86.1%
With sodium hydroxide

Dimethyldisulphide (624-92-0) + 3-fluorobromobenzene (1073-06-9) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With potassium tert-butylate In acetonitrile at 50℃; for 6h; Sealed tube;	80%

di-tert-butyl peroxide (110-05-4) + 1-bromo-3-[(3-bromophenyl)disulfanyl]benzene (19742-90-6) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
In acetonitrile at 120℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	67%

Dimethyldisulphide (624-92-0) + 1-Bromo-3-iodobenzene (591-18-4) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium hydroxide In water at 100℃; for 12h; Sealed tube;	60%
With n-butyllithium 1.) THF, -78 deg C, 2 h, 2.) THF, from -75 deg C to RT; Yield given. Multistep reaction;

Dimethyldisulphide (624-92-0) + (3-bromophenyl)boronic acid (89598-96-9) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With di-tert-butyl peroxide In acetonitrile at 120℃; for 12h; Sealed tube;	60%

Dimethyldisulphide (624-92-0) + 1,3-dibromobenzene (108-36-1) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With potassium tert-butylate In acetonitrile at 50℃; for 6h; Sealed tube;	42%

3-Bromothiophenol (6320-01-0) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With potassium hydroxide; dimethyl sulfate

3-methylmercaptoaniline (1783-81-9) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
With sulfuric acid Diazotization.Erwaermen der Diazoniumsalz-Loesung mit CuBr und KBr auf 60-70grad;

3-Bromothiophenol (6320-01-0) + dimethyl sulfate (77-78-1) → 3-bromo-1-(methylthio)benzene (33733-73-2)

6,6-dibromobicylo[3.1.0]hexane (2568-36-7) → 2-bromocyclohex-2-en-1-ol (109380-07-6, 109431-74-5, 122797-27-7, 61426-49-1) + 3-bromo-1-(methylthio)benzene (33733-73-2) + 2-bromo-1-(methylsulfanyl)benzene (19614-16-5) + 1,6-dibromocyclohex-1-ene (17202-32-3)

Conditions	Yield
In dimethyl sulfoxide at 125℃; for 0.5h; Mechanism; var. of conditions;

1,3-dibromobenzene (108-36-1) + sodium thiomethoxide (5188-07-8) → 3-bromo-1-(methylthio)benzene (33733-73-2)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 50 - 64℃; for 4h; Inert atmosphere; Large scale;

3-bromo-1-(methylthio)benzene (33733-73-2) → 1-bromo-3-methanesulfinyl-benzene (29959-92-0)

Conditions	Yield
With 1,3-dimethylalloxan; dihydrogen peroxide; magnesium sulfate In dichloromethane at 25℃; for 0.5h;	99%
With 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone In methanol at 20℃; for 6h; Irradiation;	98%
With dihydrogen peroxide; phenol for 0.00833333h;	96%

3-bromo-1-(methylthio)benzene (33733-73-2) + 2,2,2-trichloroethyl-N-methanesulfonyloxycarbamate → S-methyl-S-3-bromophenyl-N-(2,2,2-trichloroethoxycarbonyl)sulfilimine

Conditions	Yield
With 1-Butylimidazole; iron(II) chloride hydrate In ethyl acetate at 80℃; for 0.25h; Sealed tube;	99%

3-bromo-1-(methylthio)benzene (33733-73-2) + 3-phenyl-5H-1,4,2-dioxazol-5-one (19226-36-9) → (-)-N-benzoyl 3-bromophenyl methyl sulfimide

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With C61H40F4N2O3Ru In tetrahydrofuran at 25℃; for 0.5h; Molecular sieve; Schlenk technique; Inert atmosphere; Stage #2: 3-phenyl-5H-1,4,2-dioxazol-5-one In tetrahydrofuran at 25℃; for 18h; Molecular sieve; Schlenk technique; Inert atmosphere; enantioselective reaction;	99%

3-bromo-1-(methylthio)benzene (33733-73-2) + 3-methylthiophenylboronic acid (128312-11-8) → 3,3'-di(methylthio)biphenyl (10075-91-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 80℃; Suzuki-Miyaura Coupling;	98%

3-bromo-1-(methylthio)benzene (33733-73-2) → 1-bromo-3-methanesulphonylbenzene (34896-80-5)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; Stage #2: With sodium thiosulfate In dichloromethane; water	97%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;	97%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	96%

3-bromo-1-(methylthio)benzene (33733-73-2) + 4-methoxyphenylboronic acid (5720-07-0) → 4-methoxy-3'-(methylthio)-1,1'-biphenyl (95391-98-3)

Conditions	Yield
With palladium diacetate; potassium carbonate In tetrahydrofuran; water for 10h; Suzuki-Miyaura coupling; Inert atmosphere; Reflux;	97%

benzenesulfonamide (98-10-2) + 3-bromo-1-(methylthio)benzene (33733-73-2) → N-(3-(methylthio)phenyl)benzenesulfonamide (528576-23-0)

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; N,N,N',N'-tetramethylguanidine In acetonitrile at 55℃; for 48h; Temperature; Inert atmosphere; Irradiation; Glovebox;	97%

3-bromo-1-(methylthio)benzene (33733-73-2) + phenylacetylene (536-74-3) → 1-methylsulfanyl-3-(phenylethynyl)benzene

Conditions	Yield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] In water at 45℃; for 5h; Sonogashira Cross-Coupling; Inert atmosphere;	96%
With potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C64H118O20 In water at 45℃; for 6h; Sonogashira Cross-Coupling; Inert atmosphere;	91%
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride at 90℃; Sonogashira coupling;	65%

3-bromo-1-(methylthio)benzene (33733-73-2) + copper(I) cyanide (544-92-3) → 3-cyanophenyl methyl sulfide (65052-48-4)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; Product distribution; Rate constant; other solvent;	95%
In N,N-dimethyl-formamide at 150℃;

3-bromo-1-(methylthio)benzene (33733-73-2) + tert-butyldimethyl(((3-phenylpropyl)sulfonyl)methoxy)silane → methyl(3-((3-phenylpropyl)sulfonyl)phenyl)sulfane

Conditions	Yield
With copper(l) iodide; cesium fluoride; L-proline; sodium hydroxide In dimethyl sulfoxide at 95℃; for 24h;	94%

chloro-trimethyl-silane (75-77-4) + 3-bromo-1-(methylthio)benzene (33733-73-2) → trimethyl(3-(methylthio)phenyl)silane (22515-28-2)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 25℃;	93%
With magnesium In N,N,N,N,N,N-hexamethylphosphoric triamide

N,N-diethyl-2,2,2-trifluoroacetamide (360-92-9) + 3-bromo-1-(methylthio)benzene (33733-73-2) → 2,2,2-trifluoro-1-(3-methylsulfanylphenyl)ethanone

Conditions	Yield
With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h;	93%

3-bromo-1-(methylthio)benzene (33733-73-2) + bromoacetic acid methyl ester (96-32-2) → methyl 2-((3-bromophenyl)thio)acetate

Conditions	Yield
In 2,2,2-trifluoroethanol at 100℃; for 24h;	93%

3-bromo-1-(methylthio)benzene (33733-73-2) + potassium cyanide (151-50-8) → 3-cyanophenyl methyl sulfide (65052-48-4)

Conditions	Yield
With 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In benzene at 80℃; for 50h; Product distribution; Rate constant;	92%

3-bromo-1-(methylthio)benzene (33733-73-2) → (R)-1-bromo-3-(methylsulfinyl)benzene (188539-86-8)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With manganese(II) triflate; N1,N2-bis(2-((R)-4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl)benzene-1,2-diamine In acetonitrile at 20℃; for 6h; Inert atmosphere; Green chemistry; Stage #2: With 1-Adamantanecarboxylic acid; dihydrogen peroxide In isopropyl alcohol; acetonitrile at -20℃; for 2h; Inert atmosphere; Green chemistry; enantioselective reaction;	92%
With manganese(II) triflate; 1-Adamantanecarboxylic acid; C30H34N4O2; dihydrogen peroxide In water; isopropyl alcohol; acetonitrile at 20℃; for 0.0166667h; Flow reactor; enantioselective reaction;	90%
With manganese(II) triflate; C30H34N4O2; dihydrogen peroxide; acetic acid In dichloromethane; water at 0℃; for 1h; Inert atmosphere; enantioselective reaction;	80%
With titanium(IV) isopropylate; Diethyl tartrate; Cumene hydroperoxide In dichloromethane; water at -20℃; for 3h; Oxidation;	67%

3-bromo-1-(methylthio)benzene (33733-73-2) → (S)-1-bromo-3-(methylsulfinyl)benzene

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With iron(III) trifluoromethanesulfonate; C59H88N4O4 In tetrahydrofuran at 35℃; for 0.5h; Inert atmosphere; Stage #2: With dihydrogen peroxide In tetrahydrofuran; water at 25℃; for 4h; Inert atmosphere; enantioselective reaction;	92%
With Cumene hydroperoxide; titanium BINOL derivative In tetrachloromethane at 25℃; for 72h;	36.5%

6-chloro-N-(pyridin-3-ylmethyl)pyridine-3-amine + 3-bromo-1-(methylthio)benzene (33733-73-2) → 6-chloro-N-(dipyridin-3-ylmethyl)-N-[3-(methylthio)phenyl]pyridine-3-amine

Conditions	Yield
With sodium t-butanolate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane at 100℃; for 4h;	91%

3-bromo-1-(methylthio)benzene (33733-73-2) + aniline (62-53-3) → N-(3-methylthiophenyl)phenylamine (13313-45-6)

Conditions	Yield
With nickel(II) bromide trihydrate; N,N-dimethyl-cyclohexanamine; Eosin Y In 1,2-dimethoxyethane; N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;	91%

3-bromo-1-(methylthio)benzene (33733-73-2) + 9H-carbazole (86-74-8) → C19H15NS

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	89.6%

3-bromo-1-(methylthio)benzene (33733-73-2) + (S)-1-phenyl-2,2,2-trichloroethyl-N-mesyloxycarbamate (1644186-25-3) → (S)-S-methyl-S-(3-bromophenyl)-N-(((S)-2,2,2-trichloro-1-phenylethoxy)carbonyl)sulfilimine

Conditions	Yield
With dmap; tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh); 1,1’-methylenebis(4-dimethylaminopyridinium) dichloride; potassium carbonate In Isopropyl acetate; water at 23℃; for 4h; stereoselective reaction;	89%
With dmap; tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh); 1,1’-methylenebis(4-dimethylaminopyridinium) dichloride; potassium carbonate In Isopropyl acetate; water at 25℃; for 4h; diastereoselective reaction;	89%

Methyl 2-acetamidoacrylate (35356-70-8) + 3-bromo-1-(methylthio)benzene (33733-73-2) → C13H16BrNO3S

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; sodium 2,2,2-trifluoroacetate In methanol; dichloromethane at 30℃; Irradiation;	89%

3-bromo-1-(methylthio)benzene (33733-73-2) → 3-methylsulfanylphenol (3463-03-4)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); 2-((di-adamantan-1-yl)phosphaneyl)-1-(2,6-diisopropylphenyl)-1H-imidazole In 1,4-dioxane; water at 100℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 20℃; Inert atmosphere;	88%

[bis(acetoxy)iodo]benzene (3240-34-4) + 3-bromo-1-(methylthio)benzene (33733-73-2) → ((3-bromophenyl)thio)methyl acetate

Conditions	Yield
With (triphenylphosphine)gold(I) chloride In 1,2-dichloro-ethane at 130℃; Schlenk technique;	88%

CYANAMID (420-04-2) + 3-bromo-1-(methylthio)benzene (33733-73-2) → C8H7BrN2S

Conditions	Yield
With N-Bromosuccinimide; potassium tert-butylate In methanol at 20℃; for 1h;	87%
With N-Bromosuccinimide; potassium tert-butylate In methanol at 20℃; for 1h;	87%

3-bromo-1-(methylthio)benzene (33733-73-2) + methyl trifluoromethanesulfonate (333-27-7) → CF3O3S(1-)*C8H10BrS(1+)

Conditions	Yield
In 1,2-dichloro-ethane at 60℃; for 12h;	87%

2,2-dimethylmalononitrile (7321-55-3) + 3-bromo-1-(methylthio)benzene (33733-73-2) → 3-cyanophenyl methyl sulfide (65052-48-4)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With magnesium; lithium chloride In tetrahydrofuran at 23℃; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 23℃; for 0.5h;	84%
Stage #1: 3-bromo-1-(methylthio)benzene With magnesium; lithium chloride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 25℃; Inert atmosphere;	65%

3-methyl-2,5-dihydrothiophen-1,1-dioxide (1193-10-8) + 3-bromo-1-(methylthio)benzene (33733-73-2) → (Z)-methyl(3-(2-methylbuta-1,3-dien-1-yl)phenyl)sulfane

Conditions	Yield
Stage #1: 3-methyl-2,5-dihydrothiophen-1,1-dioxide With o-phenylenebis(diphenylphosphine); potassium methanolate; palladium diacetate; potassium carbonate In tetrahydrofuran at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: 3-bromo-1-(methylthio)benzene In tetrahydrofuran at 20 - 110℃; for 37.3333h; Sealed tube; diastereoselective reaction;	84%

3-bromo-1-(methylthio)benzene (33733-73-2) + tert-butyl 2-oxopyrrolidine-1-carboxylate (85909-08-6) → [4-(3-methylsulfanyl-phenyl)-4-oxo-butyl]-carbamic acid tert-butyl ester (914954-35-1)

Conditions	Yield
Stage #1: 3-bromo-1-(methylthio)benzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.66667h; Stage #2: tert-butyl 2-oxopyrrolidine-1-carboxylate In tetrahydrofuran; hexanes at -78℃; for 2h;	83%

3-bromo-1-(methylthio)benzene (33733-73-2) + iodobenzene dimethacrylate → ((3-bromophenyl)thio)methyl methacrylate

Conditions	Yield
With (triphenylphosphine)gold(I) chloride In 1,2-dichloro-ethane at 130℃; Schlenk technique;	83%

Upstream product

• 624-92-0 Dimethyldisulphide 
• 108-36-1 1,3-dibromobenzene 
• 1073-06-9 3-fluorobromobenzene 
• 2568-36-7 6,6-dibromobicylo[3.1.0]hexane 
• 6320-01-0 3-Bromothiophenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 1783-81-9 3-methylmercaptoaniline 
• 110-05-4 di-tert-butyl peroxide 
• 19742-90-6 1-bromo-3-[(3-bromophenyl)disulfanyl]benzene 
• 89598-96-9 (3-bromophenyl)boronic acid 
• 591-18-4 1-Bromo-3-iodobenzene 
• 5188-07-8 sodium thiomethoxide 

Downstream Products

• 213607-84-2 Ethyl 4-(3'-Methylthio)phenyl-4-oxobutyrate 
• 288571-53-9 3-{2-[1-Methoxy-meth-(E)-ylidene]-cyclohexyl}-1-(3-methylsulfanyl-phenyl)-propan-1-one 
• 210905-75-2 1-ethynyl-3-(methylthio)benzene 
• 433936-26-6 (2RS,3RS)-1-dimethylamino-2-methyl-3-(3-methylsulphanylphenyl)-pentan-3-ol Hydrochloride 
• 346688-57-1 1-[3-(methylsulfonyl)phenyl]piperazine 
• 346688-66-2 1-tert-butoxycarbonyl-4-hydroxy-4-[3-(methylthio)phenyl]piperidine 
• 160777-44-6 3-(3-Methanesulfonyl-phenyl)-pyridine; hydrochloride 
• 160866-61-5 3-(3-methanesulfonylphenyl)piperidine 
• 504398-38-3 C₁₂H₁₇NO₂S*C₄H₆O₆ 
• 160866-61-5 PNU 180222 
• 156907-84-5 [3H]-(-)-OSU 6162 hydrochloride 
• 914954-35-1 [4-(3-methylsulfanyl-phenyl)-4-oxo-butyl]-carbamic acid tert-butyl ester 
• 1010835-35-4 2-tert-Butyl-4-(3-methylsulfanylphenyl)-1-(tetrahydropyran-4-ylmethyl)-1H-imidazole 
• 3463-03-4 3-methylsulfanylphenol 

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